Processes Patents (Class 564/314)
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Patent number: 9196840Abstract: Novel fluoroacyl arylamines useful in organic electronic applications are disclosed, including methods of synthesizing those fluoroacyl arylamines using Lewis acids for acyl moiety activation.Type: GrantFiled: November 21, 2012Date of Patent: November 24, 2015Assignee: Xerox CorporationInventors: Adrien P Cote, Richard A Klenkler, Amanda L Bongers, Gregory M McGuire
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Publication number: 20140275561Abstract: The invention in this document is related to the field of preparation of haloalkoxyarylhydrazines and certain intermediates derived therefrom, where said intermediates are useful in the preparation of certain pesticides disclosed in U.S. Pat. No. 8,178,658.Type: ApplicationFiled: February 27, 2014Publication date: September 18, 2014Applicant: Dow AgroSciences LLCInventors: Ronald ROSS, JR., Gary ROTH
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Publication number: 20140275558Abstract: This document is related to the field of preparation of haloalkoxyarylhydrazines and certain intermediates derived therefrom, where said intermediates are useful in the preparation of certain pesticides disclosed in U.S. Pat. No. 8,178,658.Type: ApplicationFiled: February 27, 2014Publication date: September 18, 2014Applicant: Dow AgroSciences LLCInventors: Ronald ROSS, JR., Peter BORROMEO
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Patent number: 8754260Abstract: A method for making fluoroacyl arylamines is disclosed.Type: GrantFiled: November 21, 2012Date of Patent: June 17, 2014Assignee: Xerox CorporationInventors: Adrien P Cote, Amanda L Bongers
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Patent number: 8629301Abstract: The present invention relates to the economical and separation of benzphetamine hydrochloride and methamphetamine by liquid extraction. An extraction process employing a suitable organic solvent and water at a pH in the range of from about 6 to about 8 provides excellent removal of the methamphetamine by dissolution in the water phase while the benzphetamine dissolves in the organic phase. Simple separation of the two phases results in separation of the two amines.Type: GrantFiled: November 2, 2005Date of Patent: January 14, 2014Assignee: Mallinckrodt LLCInventor: Keith G. Tomazi
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Publication number: 20110313171Abstract: The present invention relates to the preparation of aryl hydrazines and their salts by treating aryl diazonium salts with triphenyl phosphine followed by hydrolysis of the resulting triphenyl-aryl hydrazyl phosphonium salt to get aryl hydrazine or its salt.Type: ApplicationFiled: January 12, 2007Publication date: December 22, 2011Inventors: Chandra Purna Ray, Sreekanth Medikonduri, Gorantla Seeta Ramanjaneyulu
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Publication number: 20110031430Abstract: Novel water soluble paramagnetic organic nanoparticles are formed by a novel method where an organic solution of an organic compound is injected into water under agitation that is maintained for a desired period of time for nanoparticle growth followed by termination of the growth by the addition of an aqueous surfactant solution. The size of the nanoparticles depends on the time between injection and addition of the surfactant solution. In embodiments of the invention, the water soluble paramagnetic organic nanoparticles can be DPPH nanoparticles, DPPH nanoparticles doped with DPPH-H, or core/shell nanoparticles where a DPPH core is covered by a DPPH-H shell.Type: ApplicationFiled: August 4, 2010Publication date: February 10, 2011Applicant: UNIVERSITY OF FLORIDA RESEARCH FOUNDATION INC.Inventors: Y. CHARLES CAO, Ou Chen, Alexander Angerhofer
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Publication number: 20100096585Abstract: This invention relates to a process for preparing 2,6-dichloro-4-(trifluoromethyl)phenylhydrazine of the formula (I) wherein a mixture comprising 1,3-dichloro-2-fluoro-5-trifluoromethylbenzene and 1,2-dichloro-3-fluoro-5-trifluoromethylbenzene is reacted with a hydrazine source selected from hydrazine, hydrazine hydrate or acid addition salts of hydrazine, optionally in the presence of at least one organic solvent.Type: ApplicationFiled: February 27, 2008Publication date: April 22, 2010Applicant: BASF SEInventors: Thomas Zierke, Michael Rack
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Publication number: 20100010263Abstract: This invention relates to a process for preparing substituted phenylhydrazines of the formula I wherein R has the meaning as indicated in the description, comprising reacting a dichlorofluorobenzene of the formula II with a hydrazine source selected from hydrazine, hydrazine hydrate and acid addition salts of hydrazine and optionally being carried out in the presence of at least one organic solvent.Type: ApplicationFiled: February 27, 2008Publication date: January 14, 2010Applicant: BASF SEInventors: Thomas Zierke, Michael Rack
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Publication number: 20080306302Abstract: A process for the preparation of organic cation tetrakis(Faryl) borate salts. The process includes preparation of intermediate, mono-hydrazine substituted (Faryl) compound, from (Faryl) compound using hydrazine at temperatures below 78° C. A stoichiometric excess of hydrazine to the (Faryl) compound to the (Faryl) compound is used. The process further includes the preparation of the organic cation tetrakis(Faryl) borate in ethereal medium.Type: ApplicationFiled: December 8, 2006Publication date: December 11, 2008Inventor: Bruce C. Berris
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Patent number: 7390929Abstract: The invention relates to a method for the continuous synthesis of monoalkyl-hydrazines with a functionalized alkyl group. The inventive method is characterized in that it comprises a step consisting in demixing a solution containing the synthesized monoalkyl-hydrazine, by reacting an anhydrous amine with monochloramine, in an organic phase and an aqueous phase with the addition of anhydrous sodium hydroxide. The invention can be used to obtain perfect selectivity in relation to monoalkyl-hydrazine without the presence of the di- and tri-substituted forms thereof. According to the invention, the staffing amine which has not reacted is collected and reused directly without any additional treatment.Type: GrantFiled: December 17, 2004Date of Patent: June 24, 2008Assignees: Isochem, Centre National de la Recherche Scientifique (CNRS), Universite Claude Bernard Lyon 1Inventors: Henri Delalu, Cécile Colas-Duriche, Jacques Berthet, Philippe Leurent
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Patent number: 7138548Abstract: A process for the preparation of a compound of formula (I): wherein Ar represents an optionally substituted aromatic carbocycle or heterocycle, and R1 and R2 independently represent hydrogen, C1-10 alkyl, C(O)C1-10 alkyl or optionally substituted aryl provided that R1 and R2 are not both hydrogen which process comprises reacting together a compound of formula (II): Ar—X??(II) wherein Ar is as defined in relation to formula (I) and X represents a leaving group with a a compound of formula (III) wherein R1 and R2 are as defined in relation to formula (I) under aqueous conditions in the presence of a Pd (II) salt, a ligand and a Group I or Group II metal hydroxide base at a pH greater than 7. Compounds of formula (I) may be hydrolysed to the corresponding hydrazine.Type: GrantFiled: October 2, 2002Date of Patent: November 21, 2006Assignee: Avecia LimitedInventors: Andrew John Blacker, David Dodman, David Anthony Jackson, Jan Michael Fielden, John Heathcote Atherton
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Patent number: 6852890Abstract: A process for the preparation of a phenylhydrazine or an inorganic acid salt thereof of the formula (1): wherein X is a hydrogen or halogen atom; Y is a halogen atom; and W is a hydrogen atom or —ZR in which Z is an oxygen or sulfur atom, and R is a hydrogen atom, an alkyl group, a haloalkyl group, and so on, by the hydrolysis of a phenylhydrazine derivative of the formula (2): where X, Y and W are the same as defined above, and the Q groups are a hydrogen atom, an ammonium group or an alkali metal atom in the presence of water and an inorganic acid, in which the concentration of the inorganic acid is at least 6 moles per 1 kg of water in a reaction system.Type: GrantFiled: March 3, 2000Date of Patent: February 8, 2005Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuyuki Tanaka, Yoshiaki Oda
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Patent number: 6720428Abstract: According to a novel process, microbicidally active 2-(1,2,4-triazol-1-yl)-ethanols of the formula in which A1, A2, R1, R2, R3 and R4 are as defined in the description, can be prepared by reacting hydrazine derivatives of the formula with N-dihalogenomethyl-formamidinium halide of the formula in which X represents chlorine or bromine, if appropriate in the presence of a diluent.Type: GrantFiled: August 6, 2002Date of Patent: April 13, 2004Assignee: Bayer AktiengesellschaftInventor: Thomas Himmler
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Patent number: 6706895Abstract: Disclosed herein is a compound having the formula: wherein R1 is alkyl and R2 and R3 are independently selected aryl groups. Also disclosed is a method of making bifenazate using the compound as an intermediate.Type: GrantFiled: November 14, 2002Date of Patent: March 16, 2004Assignees: Uniroyal Chemical Company, Inc., Crompton Co./CieInventors: Sheldon B. Park, Gaik-Lean Chee, Mark A. Dekeyser
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Patent number: 6509503Abstract: The invention relates to processes for the preparation of compounds of formula (I) wherein R1 and R2 each independently represent a halogen atom.Type: GrantFiled: May 3, 2002Date of Patent: January 21, 2003Assignee: Aventis Cropscience S.A.Inventors: Jean-Erick Angel, Gilles Perrin-Janet, Pierre Leroy
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Patent number: 6489512Abstract: A method for making an indole compound includes transition metal-catalyzed arylation of a hydrazone to form an aryl hydrazone, hydrolysis of the aryl hydrazone to form an aryl hydrazine, and acid catalyzed cyclization of the aryl hydrazine to form the indole compound.Type: GrantFiled: June 21, 2002Date of Patent: December 3, 2002Assignee: Rhodia Chirex Inc.Inventors: Frederick Hicks, Da-Ming Gou, Salvatore Anthony Marchese, Lawrence J. Martel, Atena Necula, Richard E. Benetti, Richard A. Silva
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Publication number: 20020115880Abstract: A process for preparing 4-substituted 2-alkylbiphenyls and 2-alkoxybiphenyls of the formula (I), 1Type: ApplicationFiled: February 11, 2002Publication date: August 22, 2002Applicant: Clariant GmbHInventors: Andreas Meudt, Stefan Scherer, Frank Vollmuller, Heinz Georg Kautz
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Publication number: 20020082274Abstract: This invention relates to methods of preparing sodium-hydrogen exchanger type 1 (NHE-1) inhibitors of formula I′ 1Type: ApplicationFiled: November 27, 2001Publication date: June 27, 2002Inventors: John F. Lambert, Timothy Norris
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Patent number: 6278022Abstract: Disclosed herein is an improvement in a method for making compounds having the structural formulae (I) or (II): wherein: X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from C1-C4 alkoxy; hydroxyl; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl; Y is H, C1-C4 alkanoyl, C1-C4 haloalkenoyl, dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or C1-C4 alkoxy carbonyl; and R is H, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C3-C6 cycloalkyl; and Z is O or S, wherein the improvement comprises the steps of: A) selecting as a starting material a compound of the structural formula B) dissolving compound III in an organic solvent selected from the groupType: GrantFiled: November 1, 1999Date of Patent: August 21, 2001Assignee: CK Witco CorporationInventor: Haihong Jin
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Patent number: 6166243Abstract: Disclosed herein is a method for making compounds having the structural formulae (I) or (II): ##STR1## wherein: X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from C.sub.1 -C.sub.4 alkoxy; hydroxyl; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl; Y is H, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 haloalkanoyl dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or C.sub.1 -C.sub.4 alkoxy carbonyl; and R is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C.sub.3 -C.sub.Type: GrantFiled: November 1, 1999Date of Patent: December 26, 2000Assignee: CK Witco CorporationInventors: Haihong Jin, Joseph A. Feiccabrino
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Patent number: 6087534Abstract: The invention involves a procedure for synthesizing aryl hydrazine through reduction of a diazo derivative. The distinguishing feature of the method is that it involves at least the following step: c) bringing a diazo derivative into contact with a sulphite solution in which the pH level is at least 7. Applications: organic synthesis.Type: GrantFiled: September 21, 1998Date of Patent: July 11, 2000Assignee: Rhodia ChimieInventors: Jean-Manuel Mas, Christophe Rochin
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Patent number: 6057478Abstract: The present invention relates to a process for preparing arylhydrazines of the formula R.sup.1 R.sup.2 R.sup.3 Ar--NH--NH.sub.2 (I) by reacting an arylhydrazinedisulfonate of the formula ##STR1## in which R.sup.1, R.sup.2, and R.sup.3 are identical or different and are H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or OH, Ar is phenyl or naphthyl, M.sup.1 and M.sup.2 are identical or different and are H, NH.sub.4, an alkali metal or 1/2 alkaline earth metal and R.sup.1, R.sup.2, R.sup.3 and Ar in the formulae (I) and (II) have the same meaning, with water and an inorganic acid at from 0 to 100.degree. C. in the presence of an inert organic solvent to give the corresponding arylhydrazine salt and treating the arylhydrazine salt with a base.Type: GrantFiled: May 18, 1999Date of Patent: May 2, 2000Assignee: Clariant GmbHInventors: Thomas Schach, Heinrich Volk, Manfred Koch
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Patent number: 5599992Abstract: The invention relates to a process for the preparation of 2-fluorophenylhydrazine or 2-fluorophenylhydrazine hydrochloride, which comprises diazotizing 2-fluoroaniline, reducing the resulting diazonium salt with alkaline bisulfite solution to give 2-fluorophenylhydrazine .alpha..beta.-disulfonate, hydrolyzing the latter with hydrochloric acid to give 2-fluorophenylhydrazine hydrochloride, adding alkali metal solution to neutralize the mixture, subsequently cooling the mixture, removing the 2-fluorophenylhydrazine precipitate by filtration and, if appropriate, reacting the latter with hydrochloric acid to give 2-fluorophenylhydrazine hydrochloride.Type: GrantFiled: January 22, 1996Date of Patent: February 4, 1997Assignee: Hoechst AktiengesellschaftInventor: Otto Arndt
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Patent number: 5585521Abstract: Alkylhydrazine salts are prepared on an industrial scale and with good results by reacting together hydrazine, an alkene and a strong protonic acid in the presence of water, hydrazine and the protonic acid being introduced, the alkene being added, the liquid and gaseous phases present in the reaction vessel being intensively mixed together at 75.degree. to 150.degree. C., then the reaction mixture being cooled to temperatures below 60.degree. C., the precipitated alkylhydrazine salt being separated off, hydrazine and strong protonic acid being again added to the mother liquor, then alkene being added again and the next reaction cycle being thus carried out.Type: GrantFiled: September 22, 1995Date of Patent: December 17, 1996Assignee: Bayer AktiengesellschaftInventors: Wolfram Eichinger, Helmut Fiege
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Patent number: 5489711Abstract: An oligomer from diarylamines is disclosed which has desirable antioxidant properties in lubricating oils which contain synthetic ester lubricants. The oligomer is desirable for use at higher temperatures where it has less volatility than simple diarylamines. The oligomer has substantial portions of monosubstituted diphenylamine repeat units which result in linear oligomers. Di and polysubstituted diphenylamines may optionally be present as repeat units. These di and polysubstituted diphenylamines generally react as monofunctional reactants in oligomerization and tend to reduce the number of repeat units in the average oligomer.Type: GrantFiled: December 20, 1994Date of Patent: February 6, 1996Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 5387725Abstract: Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.Type: GrantFiled: July 12, 1993Date of Patent: February 7, 1995Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Katherine S. Clement, Steven L. Brewster, Emmett L. Tasset, Paul M. Puckett, V. Rao Durvasula, Hong A. Nguyen
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Patent number: 5041667Abstract: A process for producing a chlorohenylhydrazine compound is disclosed, which comprises chlorinating at least one hydrogen atom on the phenyl nucleus in a beta-imidated phenylhydrazine compound and subsequently hydrolyzing the chlorinated compound. Said chlorophenylhydrazine compound is useful as starting material for the production of herbicide, insecticide and photographic coupler is produced in high yield and low cost.Type: GrantFiled: June 26, 1986Date of Patent: August 20, 1991Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Mitsuto Fujiwhara, Tamotsu Kojima
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Patent number: 5001262Abstract: This invention describes a method for synthesizing a polyhaloaromatic hydrazine compound, such as a tetra- or a penta- halophenylhydrazine. Such compounds are useful in the preparation of photographic color couplers.Type: GrantFiled: June 26, 1989Date of Patent: March 19, 1991Assignee: Eastman Kodak CompanyInventor: Michael W. Crawley
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Patent number: 4987258Abstract: The invention relates to 4,4'-diaminodiphenyl compounds of the formula I ##STR1## in which X denotes the n-propyl, isopropyl, n-butyl, isobutyl, 1-methylpropyl, n-propoxy, isopropoxy, isobutoxy, 1-methylpropoxy or 2-methoxyethoxy radical and A is 0 or the equivalent of an inorganic acid.The preparation is effected by reducing ortho-X-substituted nitrobenzene and benzidine rearrangement of the resulting hydrazobenzene derivative. The compounds of the formula (I) are suitable for use as components in the preparation of dyes and pigments.Type: GrantFiled: February 20, 1987Date of Patent: January 22, 1991Assignee: Hoechst AktiengesellschaftInventors: Klaus Hunger, Heinrich Frolich, Kurt C. Habig
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Patent number: 4864032Abstract: A process for the preparation of aryl hydrazines and indazoles by reacting organometallic regents with azodicarboxylates.Type: GrantFiled: July 2, 1987Date of Patent: September 5, 1989Assignee: Ortho Pharmaceutical CorporationInventor: James P. Demers
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Patent number: 4855501Abstract: Disclosed is a process for the preparation of monomethylhydrazine which comprises reacting hydrazine monohydrochloride with methanol in the presence of hydrazine dihydrochloride or methyl chloride and recovering free monomethylhydrazine from the formed monomethylhydrazine hydrochloride.According to this process, monomethylhydrazine can be prepared at a high selectivity very easily while controlling formation of by-products.Type: GrantFiled: December 3, 1981Date of Patent: August 8, 1989Assignee: Japan Hydrazine Co., Inc.Inventors: Shiro Hojo, Yoichi Hasegawa, Takeo Hirai
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Patent number: 4772747Abstract: Disclosed is a process for the preparation of 2,4,6-trichlorophenylhydrazine by chlorinating the reaction product of phenylhydrazine and a dicarboxylic anhydride to obtain an N-(2,4,6-trichloroanilino)dicarboximide which is reacted with a base capable of liberating 2,4,6-trichlorophenylhydrazine therefrom.Type: GrantFiled: October 28, 1983Date of Patent: September 20, 1988Assignee: Eastman Kodak CompanyInventors: Kevin J. Edgar, John A. Hyatt
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Patent number: 4628119Abstract: A process for preparing hydrazine hydrohalogenide is disclosed.Type: GrantFiled: February 19, 1985Date of Patent: December 9, 1986Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Takanari Nawata, Shuzabu Sakaguchi, Osamu Aoki
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Patent number: 4574155Abstract: This invention provides a process for preparing a 2-hydrazino-1,3-diazacycloalk-2-ene hydrohalide. The process comprises reacting a one molar proportion of either tautomeric isomer of a 2-nitroamino-1,3-diazacycloalk-2-ene represented by the following formulas: ##STR1## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxyalkyl, phenyl, substituted phenyl, benzyl, or substituted benzyl, R.sup.2 and R.sup.3 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxyalkyl, hydroxyl, aryl, substituted aryl, aralkyl and substituted aralkyl, and n is an integer from 0 to 3 with about an equimolar proportion of an ammonium halide or hydrazonium halide, and about a 1 to 2 molar proportion of hydrazine hydrate in a composition selected from a C.sub.1 to C.sub.4 aliphatic alcohol, water or a mixture thereof, at a temperature from about ambient to the reflux, and isolating the end product as a monohydrohalide.Type: GrantFiled: March 8, 1984Date of Patent: March 4, 1986Assignee: American Cyanamid CompanyInventor: Thurairajah Padmanathan
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Patent number: 4564677Abstract: Disclosed is a method of preparing N-amino compounds from corresponding secondary amines by reacting a secondary amine with nitrous acid and zinc in a neutral pH reaction media to form the corresponding N-amine.Type: GrantFiled: January 19, 1984Date of Patent: January 14, 1986Assignee: USV Pharmaceutical Corp.Inventor: Martin L. Kantor
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Patent number: 4352941Abstract: Crude phenylhydrazine is distilled in the presence of a glycol to obtain phenylhydrazine of high purity in a high yield.Type: GrantFiled: June 28, 1978Date of Patent: October 5, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Shinichi Hasegawa, Yuji Ueda, Hiroshige Tomita
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Patent number: 4286108Abstract: A process is disclosed for preparing anhydrous hydrazines by reacting a tertiary hydrazinium halide with a corresponding alkali metal or alkaline earth metal amide in the presence of a non-aqueous inert carrier.Type: GrantFiled: October 17, 1979Date of Patent: August 25, 1981Inventor: Hans Osborg