Abstract: Processes for preparing &agr;-substituted benzylnitroguanidines include the steps of providing a reaction mixture comprising water, alcohol, an S-alkyl nitroisothiourea, and an &agr;-substituted benzylamine; heating the reaction mixture; steam distilling the alcohol from the reaction mixture; and isolating an &agr;-substituted benzylnitroguanidine from the remaining water layer.
Type:
Grant
Filed:
June 20, 2002
Date of Patent:
January 20, 2004
Assignee:
Bayer Cropscience LP
Inventors:
David M. Mayes, Vijay C. Desai, Eric Rivadeneira
Abstract:
The subject invention involves novel acyl isothiocyanate resins of formula (I) and processes for making them: (a) starting with a phenyl carboxy resin, treating the resin with any reagent that converts the carboxy to an acyl halide, followed by treatment with tetranikylammonium thiocyanate or an alkali metal salt thereof, to provide the acyl isothiocyanate resin. The subject invention also involves processes for making guanidine compounds and related cyclized compounds using an acyl isothiocyanate resin, comprising the following steps: (b) reacting the acyl isothiocyanate resin with a primary amine; (c) reacting the product from Step (b) with a sulfur activating agent and ammonia or a primary or secondary amine; (d) treating the product from Step (c) with a strong base or medium strength acid to cleave product from the resin, providing the guanidine compound or/and the related cyclized compound.
Abstract: An improved method for guanylating amines is provided. Broadly, the amines are reacted with a guanylating agent in the presence of a nickel catalyst. Preferably, the nickel catalyst comprises nickel in the zero oxidation state. Suitable nickel(0) catalysts are derived from nickel-boride alloys, nickel-phosphide alloys, aluminum-nickel alloys, nickel on kieselguhr, and nickel on silica/alumina catalysts. Preferred guanylating agents are thioureas and isothioureas. In one embodiment, protecting groups are selectively attached to the guanylating agents to yield particular substituted guanidines. The preferred protecting groups are Boc groups, Cbz groups, and arylsulfonyl groups. The reactions are particularly well suited for guanylating primary and secondary amines. The methods of the invention can be carried out under ambient conditions to provide high yields of the corresponding guanidines, with the nickel catalyst being essentially completely recoverable for reuse.
Abstract: Substituted guanidine derivatives of the formula I ##STR1## are prepared by a) converting urea into an alkylated isourea of the formula II ##STR2## and b) reacting the alkylated isourea with a primary or secondary amine of the formula III ##STR3## where the substituents R.sup.1, R.sup.2 and R.sup.10 have the meanings explained in the description.
Type:
Grant
Filed:
October 27, 1998
Date of Patent:
July 25, 2000
Assignee:
BASF Aktiengesellschaft
Inventors:
Thomas Greindl, Gunter Scherr, Rolf Schneider, Klaus Mundinger
Abstract: The present invention provides a process for making 2-amino-2-imidazoline, guanidine, and 2-amino-3,4,5,6-tetrahydroyrimidine derivatives by preparing the corresponding activated 2-thio-subsituted-2-derivative in a two-step, one-pot procedure and by further reacting yields this isolated derivative with the appropriate amine or its salts in the presence of a proton source. The present process allows for the preparation of 2-amino-2-imidazolines, quanidines, and 2-amino-3,4,5,6-tetrahydropyrimidines under reaction conditions that eliminate the need for lengthy, costly, or multiple low yielding steps, and highly toxic reactants. This process allows for improved yields and product purity and provides additional synthetic flexibility.
Type:
Grant
Filed:
November 25, 1997
Date of Patent:
May 23, 2000
Assignee:
The Procter & Gamble Company
Inventors:
Michael Selden Godlewski, Sean Rees Klopfenstein, Sreenivasa Reddy Mundla, William Lee Seibel, Randy Stuart Muth
Abstract: A process for the preparation of aromatic N,N'-disubstituted guanidines is described in which the corresponding aromatic N,N'-disubstituted thioureas are reacted with ammonia and oxygen or with an oxygen-containing gas, in the presence of a solvent and elements acting as catalysts having atomic numbers 21 through 30 in the Periodic Table or the lanthanides or the salts, oxides or complexes thereof.
Type:
Grant
Filed:
January 17, 1986
Date of Patent:
February 6, 1990
Assignee:
Akzo N.V.
Inventors:
Manfred Bergfeld, Ludwig Eisenhuth, Hans Zengel
Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.