Patents by Inventor Sebastian Peer Smidt
Sebastian Peer Smidt has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 8592578Abstract: The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylic acids and their esters, 2-(aminomethylidene)-4,4-difluoro-3-oxobutteric esters of the formula (I) in which R1, R2 and R3 independently of one another are C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C10-cycloalkyl or benzyl or NR2R3 is a 5- to 10-membered heterocyclic radical, to a process for preparing compounds of the formula (I) wherein an appropriate 3-aminoacrylic ester is reacted with difluoroacetyl fluoride and to the use of compounds of the formula (I) in the process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylic acids and their esters.Type: GrantFiled: October 17, 2012Date of Patent: November 26, 2013Assignee: BASF SEInventors: Thomas Zierke, Volker Maywald, Michael Rack, Sebastian Peer Smidt, Michael Keil, Bernd Wolf, Christopher Koradin
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Patent number: 8586750Abstract: The present invention relates to a process for preparing 2-(aminomethylidene)-4,4-dihalo-3-oxobutyric esters of the formula (I), wherein R1, R2, R3 are C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C10-cycloalkyl or benzyl, and/or R2 together with R3 and the nitrogen atom to which the two radicals are attached are a heterocyclic radical, in which a corresponding 3-aminoacrylic ester is reacted with a halogen-substituted acetyl fluoride in the presence of at least one alkali or alkaline earth metal fluoride; and the further conversion of halogen-substituted 2-(aminomethylidene)-3-oxobutyric esters of the formula (I) to halomethyl-substituted pyrazol-4-ylcarboxylic acids and their esters.Type: GrantFiled: April 30, 2009Date of Patent: November 19, 2013Assignee: BASF SEInventors: Thomas Zierke, Volker Maywald, Michael Rack, Sebastian Peer Smidt, Michael Keil, Bernd Wolf, Christopher Koradin
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Patent number: 8492558Abstract: The present invention relates to a process for preparing 2-aminobiphenyls of the formula I in which n is 0, 1, 2 or 3, R1 is hydrogen, cyano or fluorine, and each R2 is independently selected from cyano, fluorine, C1-C4-alkyl, C1-C4-fluoroalkyl, C1-C4-alkoxy, C1-C4-fluoroalkoxy, C1-C4-alkylthio and C1-C4-fluoroalkylthio. The invention also relates to a process for preparing pyrazolecarboxamides of such 2-aminobiphenyls.Type: GrantFiled: February 18, 2010Date of Patent: July 23, 2013Assignee: BASF SEInventors: Thomas Zierke, Volker Maywald, Sebastian Peer Smidt
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Patent number: 8461390Abstract: A process for preparing substituted biphenyls of the formula I where R1=nitro or amino, R2=cyano, halogen, C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylthio, n=from 0 to 3, and R3=hydrogen, cyano or halogen, which comprises reacting a halobenzene of the formula II in which Hal is chlorine or bromine, in the presence of a base and of a palladium catalyst which consists of palladium and a bidentate phosphorus ligand of the formula III where Ar is phenyl which is substituted if desired and R4 and R5 are each C1-C8-alkyl or C3-C6-cycloalkyl or together form a 2- to 7-membered bridge which may, if desired, bear a C1-C6-alkyl substituent, in a solvent or diluent, with a phenylboronic acid IVa a diphenylborinic acid IVb or a mixture of IVa and IVb.Type: GrantFiled: June 22, 2009Date of Patent: June 11, 2013Assignee: BASF SEInventors: Sebastian Peer Smidt, Volker Maywald, Kathrin Wissel-Stoll, Joachim Schmidt-Leithoff, Ansgar Gereon Altenhoff, Michael Keil
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Patent number: 8350046Abstract: A process for preparing arylcarboxamides of the formula (I) where Ar=a mono- to trisubstituted phenyl, pyridyl or pyrazolyl ring, where the substituents are selected from halogen, C1-C4-alkyl and C1-C4-haloalkyl; M=thienyl or phenyl, which may bear a halogen substituent; Q=direct bond, cyclopropylene, fused bicyclo[2.2.1]heptane or bicyclo[2.2.1]heptene ring; R1=hydrogen, halogen, C1-C6-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, mono- to trisubstituted phenyl, where the substituents are selected from halogen and trifluoromethylthio, or cyclopropyl; by reacting an acid chloride of the formula (II) with an arylamine (III) in a suitable nonaqueous solvent, wherein, in the absence of an auxiliary base, a) the acid chloride (II) is initially charged, b) a pressure of from 0 to 700 mbar is established, c) the arylamine (III) is metered in an approximately stoichiometric amount and d) the product of value is isolated.Type: GrantFiled: May 6, 2009Date of Patent: January 8, 2013Assignee: BASF SEInventors: Wolfgang Reichert, Christopher Koradin, Sebastian Peer Smidt, Volker Maywald, Bernd Wolf, Michael Rack, Thomas Zierke, Michael Keil
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Patent number: 8344157Abstract: A process for preparing 1,3-disubstituted pyrazolecarboxylic esters of the formula (I) where X, Y, Z=hydrogen or halogen and R1=C1-C6-alkyl, by metering an enol ether of the formula III where R2 is C1-C6-alkyl at from (?41) to (?80)° C. into an alkyl hydrazine of the formula II H2N—NH-lower alkyl ??(II).Type: GrantFiled: July 10, 2009Date of Patent: January 1, 2013Assignee: BASF SEInventors: Bernd Wolf, Sebastian Peer Smidt, Volker Maywald, Christopher Koradin, Michael Keil, Thomas Zierke, Michael Rack
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Patent number: 8314233Abstract: The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylic acids and their esters, 2-(aminomethylidene)-4,4-difluoro-3-oxobutteric esters of the formula (I) in which R1, R2 and R3 independently of one another are C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C10-cycloalkyl or benzyl or NR2R3 is a 5- to 10-membered heterocyclic radical, to a process for preparing compounds of the formula (I) wherein an appropriate 3-aminoacrylic ester is reacted with difluoroacetyl fluoride and to the use of compounds of the formula (I) in the process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylic acids and their esters.Type: GrantFiled: April 30, 2009Date of Patent: November 20, 2012Assignee: BASF SEInventors: Thomas Zierke, Volker Maywald, Michael Rack, Sebastian Peer Smidt, Michael Keil, Bernd Wolf, Christopher Koradin
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Patent number: 8207354Abstract: A process for preparing alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrates (VI) where R is methyl or ethyl, from crude reaction mixtures of alkyl 4,4-difluoroacetoacetates (I) by a) reacting ?where M is a sodium or potassium ion, and ?without additional solvent to form an enolate (V) b) releasing the corresponding alkyl 4,4-difluoroacetoacetate (I) from the enolate (V) by means of acid, c) removing the salt formed from cation M and acid anion as a solid and d) converting (I), without isolation from the crude reaction mixture, to the alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrate (VI), and the use of (VI) for preparing 1-methyl-3-difluoromethyl-pyrazol-3-ylcarboxyates VIIType: GrantFiled: February 27, 2009Date of Patent: June 26, 2012Assignee: BASF SEInventors: Volker Maywald, Sebastian Peer Smidt, Bernd Wolf, Christopher Koradin, Thomas Zierke, Michael Rack, Michael Keil
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Patent number: 8188295Abstract: The present invention relates to a process for preparing 3-difluoromethyl-Substituted pyrazole compounds of the formula (I) in which R1 is H, halogen, nitro, C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, phenyl, naphthyl, hetaryl, cyano, —C(?O)—OR1a, —C(?O)—NR1bR1c, —C(?O)—SR1d or —C(?S)—SR1e; R2 is H, C1-C4-alkyl, benzyl or phenyl; R3 is H, halogen, C1-C8-alkoxy, C1-C8-haloalkoxy, C3-C8-cycloalkoxy, C2-C8-alkenyloxy, C1-C8-alkylthio, C1-C8-haloalkylthio, C3-C8-cyclo-alkylthio or C2-C8-alkenylthio; compounds of the formula (II.a) or (II.b), in which R1 and R3 each have one of the definitions given above; R4 is halogen, —OR4a, —SR4a, —O—SO2—R4a or an —NR4bR4c group; R5 and R6 are each C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, benzyl or phenyl, or, together with the nitrogen atom to which they are bonded, are a 3- to 8-membered heterocycle; Lewis acid adducts of compounds of the formula (II.b); the use of compounds of the formula (II.a) or (II.Type: GrantFiled: June 13, 2008Date of Patent: May 29, 2012Assignee: BASF SEInventors: Markus Nett, Thomas Grote, Jan Klaas Lohmann, Jochen Dietz, Sebastian Peer Smidt, Michael Rack, Thomas Zierke
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Patent number: 8153820Abstract: The present invention relates to a process for preparing N-substituted (3-dihalomethylpyrazol-4-yl)carboxamides of the formula (I) in which R1 is optionally substituted phenyl or C3-C7-cycloalkyl, R1a is hydrogen or fluorine, or R1a together with R1 is optionally substituted C3-C5-alkanediyl or C5-C7-cycloalkanediyl, R2 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C4-alkoxy-C1-C2-alkyl, X is F or Cl and n is 0, 1, 2 or 3; which comprises A) providing a compound of the formula (II) in which X is F or Cl, Y is Cl or Br and R2 has one of the meanings given above and B) reacting a compound of the formula (II) with carbon monoxide and a compound of the formula (III) in which R1, R1a and n have one of the meanings given above; in the presence of a palladium catalyst; to intermediates used for the preparation according to the process according to the invention, and also to processes for their preparation.Type: GrantFiled: May 30, 2008Date of Patent: April 10, 2012Assignee: BASF SEInventors: Thomas Zierke, Joachim Rheinheimer, Michael Rack, Sebastian Peer Smidt, Ansgar Gereon Altenhoff, Joachim Schmidt-Leithoff, Nina Challand
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Patent number: 8115012Abstract: The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylates of the formula I in which R1 is C1-C8-alkyl, C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, etc.; and R2 is hydrogen, C1-C4-alkyl, benzyl or phenyl, wherein a) a compound of the general formula II in which X is fluorine, chlorine or bromine, R1 has one of the meanings given above and R4 is C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, benzyl or phenyl, is reacted with a silane compound of the general formula R3nSiCl(4-n) in which n is 1, 2 or 3 and the substituents R3 are independently of one another selected from the group consisting of C1-C8-alkyl and phenyl and with a metal selected from the metals of groups 1, 2, 3, 4 and 12 of the Periodic Table of the Elements having a redox potential of less than ?0.7 V, based on a normal hydrogen electrode (at 25° C. and 101.Type: GrantFiled: November 2, 2007Date of Patent: February 14, 2012Assignee: BASF SEInventors: Martin Sukopp, Michael Rack, Sebastian Peer Smidt, Sandra Löhr, Michael Keil, Jochen Dietz, Joachim Rheinheimer, Thomas Grote, Thomas Zierke, Jan Klaas Lohmann
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Patent number: 8101780Abstract: The present invention relates to a new crystalline form of 3-(Difluormethyl)-1-methyl-N-(3?,4?,5?-trifluor[1,1?-biphenyl]-2-yl)-1H-pyrazol-4-carboxamide. The invention also relates to processes for the production of this crystalline form and formulations for plant protection which contain the crystalline form of 3-(Difluormethyl)-1-methyl-N-(3?,4?,5?-trifluor[1,1?-biphenyl]-2-yl)-1H-pyrazol-4-carboxamide.Type: GrantFiled: July 7, 2008Date of Patent: January 24, 2012Assignee: BASF SEInventors: Heidi Emilia Saxell, Jochen Dietz, Sebastian Peer Smidt, Cedric Dieleman
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Publication number: 20110301356Abstract: The present invention relates to a process for preparing 2-aminobiphenyls of the formula I in which n is 0, 1, 2 or 3, R1 is hydrogen, cyano or fluorine, and each R2 is independently selected from cyano, fluorine, C1-C4-alkyl, C1-C4-fluoroalkyl, C1-C4-alkoxy, C1-C4-fluoroalkoxy, C1-C4-alkylthio and C1-C4-fluoroalkylthio. The invention also relates to a process for preparing pyrazolecarboxamides of such 2-aminobiphenyls.Type: ApplicationFiled: February 18, 2010Publication date: December 8, 2011Applicant: BASF SEInventors: Thomas Zierke, Volker Maywald, Sebastian Peer Smidt
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Patent number: 8030527Abstract: A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C-6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R.sup.Type: GrantFiled: March 17, 2010Date of Patent: October 4, 2011Assignee: BASF SEInventors: Sebastian Peer Smidt, Jochen Dietz, Michael Keil, Thomas Grote
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Publication number: 20110118474Abstract: A process for preparing 1,3-disubstituted pyrazolecarboxylic esters of the formula (I) where X, Y, Z=hydrogen or halogen and R1=C1-C6-alkyl, by metering an enol ether of the formula III where R2 is C1-C6-alkyl at from (?41) to (?80)° C. into an alkyl hydrazine of the formula II H2N—NH-lower alkyl ??(II).Type: ApplicationFiled: July 10, 2009Publication date: May 19, 2011Applicant: BASF SEInventors: Bernd Wolf, Sebastian Peer Smidt, Volker Maywald, Christopher Koradin, Michael Keil, Thomes Zierke, Michael Rack
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Publication number: 20110105766Abstract: A process for preparing substituted biphenyls of the formula I where R1=nitro or amino, R2=cyano, halogen, C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylthio, n=from 0 to 3, and R3=hydrogen, cyano or halogen, which comprises reacting a halobenzene of the formula II in which Hal is chlorine or bromine, in the presence of a base and of a palladium catalyst which consists of palladium and a bidentate phosphorus ligand of the formula III where Ar is phenyl which is substituted if desired and R4 and R5 are each C1-C8-alkyl or C3-C6-cycloalkyl or together form a 2- to 7-membered bridge which may, if desired, bear a C1-C6-alkyl substituent, in a solvent or diluent, with a phenylboronic acid IVa a diphenylborinic acid IVb or a mixture of IVa and IVb.Type: ApplicationFiled: June 22, 2009Publication date: May 5, 2011Applicant: BASF SEInventors: Sebastian Peer Smidt, Volker Maywald, Kathrin Wissel-Stoll, Joachim Schmidt-Leithoff, Ansgar Gereon Altenhoff, Michael Keil
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Publication number: 20110054183Abstract: A process for preparing arylcarboxamides of the formula (I) where Ar =a mono- to trisubstituted phenyl, pyridyl or pyrazolyl ring, where the substituents are selected from halogen, Ci-C4-alkyl and C1-C4-haloalkyl; M =thienyl or phenyl, which may bear a halogen substituent; Q =direct bond, cyclopropylene, fused bicycio[2.2.1]heptane or bicyclo[2.2.1]heptene ring; R1 =hydrogen, halogen, C1-C6-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, mono- to trisubstituted phenyl, where the substituents are selected from halogen and trifluoromethylthio, or cyclopropyl; by reacting an acid chloride of the formula (II) with an arylamine (III) in a suitable nonaqueous solvent, wherein, in the absence of an auxiliary base, a) the acid chloride (II) is initially charged, b) a pressure of from 0 to 700 mbar is established, c) the arylamine (III) is metered in in an approximately stoichiometric amount and d) the product of value is isolated.Type: ApplicationFiled: May 6, 2009Publication date: March 3, 2011Inventors: Wolfgang Reichert, Christopher Koradin, Sebastian Peer Smidt, Volker Maywald, Bernd Wolf, Michael Rack, Thomas Zierke, Michael Keil
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Publication number: 20110046371Abstract: The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylic acids and their esters, 2-(aminomethylidene)-4,4-difluoro-3-oxobutteric esters of the formula (I) in which R1, R2 and R3 independently of one another are C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C10-cycloalkyl or benzyl or NR2R3 is a 5- to 10-membered heterocyclic radical, to a process for preparing compounds of the formula (I) wherein an appropriate 3-aminoacrylic ester is reacted with difluoroacetyl fluoride and to the use of compounds of the formula (I) in the process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylic acids and their esters.Type: ApplicationFiled: April 30, 2009Publication date: February 24, 2011Applicant: BASF SEInventors: Thomas Zierke, Volker Maywald, Michael Rack, Sebastian Peer Smidt, Michael Keil, Bernd Wolf, Christopher Koradin
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Publication number: 20110040096Abstract: The present invention relates to a process for preparing 2-(aminomethylidene)-4,4-dihalo-3-oxobutyric esters of the formula (I), wherein R1, R2, R3 are C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C10-cycloalkyl or benzyl, and/or R2 together with R3 and the nitrogen atom to which the two radicals are attached are a heterocyclic radical, in which a corresponding 3-aminoacrylic ester is reacted with a halogen-substituted acetyl fluoride in the presence of at least one alkali or alkaline earth metal fluoride; and the further conversion of halogen-substituted 2-(aminomethylidene)-3-oxobutyric esters of the formula (I) to halomethyl-substituted pyrazol-4-ylcarboxylic acids and their esters.Type: ApplicationFiled: April 30, 2009Publication date: February 17, 2011Applicant: BASF SEInventors: Thomas Zierke, Volker Maywald, Michael Rack, Sebastian Peer Smidt, Michael Keil, Bernd Wolf, Christopher Koradin
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Publication number: 20110004002Abstract: A process for preparing alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrates (VI) where R is methyl or ethyl, from crude reaction mixtures of alkyl 4,4-difluoroacetoacetates (I) by a) reacting where M is a sodium or potassium ion, and without additional solvent to form an enolate (V) b) releasing the corresponding alkyl 4,4-difluoroacetoacetate (I) from the enolate (V) by means of acid, c) removing the salt formed from cation M and acid anion as a solid and d) converting (I), without isolation from the crude reaction mixture, to the alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrate (VI), and the use of (VI) for preparing 1-methyl-3-difluoromethyl-pyrazol-3-ylcarboxyates VIIType: ApplicationFiled: February 27, 2009Publication date: January 6, 2011Applicant: BASF SEInventors: Volker Maywald, Sebastian Peer Smidt, Bernd Wolf, Christopher Koradin, Thomas Zierke, Michael Rack, Michael Keil