Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1986-12-23
1990-07-31
Schwartz, Richard A.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
558432, 558433, 558434, 558440, 544 584, 544163, 544334, 544335, 544402, 540607, 540610, 546315, 546328, 548540, C07C11900, C07D27912, C07D26530
Patent
active
049451774
DESCRIPTION:
BRIEF SUMMARY
The invention pertains to antimicrobially active 2,2-dibromo-3-oxonitriles of Formula I, aliphatic, cycloaliphatic, aromatic or heterocyclic group, with the exception of a phenyl group substituted with 1 to 3 chlorine atoms.
The invention also pertains to a process for producing 2,2-dibromo-3-oxonitriles of Formula I, in which a carboxylic acid ester of Formula II, represents a straight chain or branched alkyl group with 1 to 4 carbon atoms, is reacted with acetonitrile in the presence of a strong base, the 3-oxonitrile produced is isolated from the reaction mixture and reacted with bromine in a solvent inert to bromine and in the presence of a hydrogen bromide acceptor, possibly under cooling, and the 2,2-dibromo-3-oxonitrile of Formula I produced is isolated from the reaction mixture.
From Chemical Abstracts, Abstract No. 84:164406x (1976), compounds of Formula I are known, in which R represents a phenyl group substituted with 1 to 3 chlorine atoms; this literature reference contains no mention of the antimicrobial activity of this class of substances.
The use of the 2,2-dibromo-3-oxonitriles of Formula I as antimicrobial active ingredients is not claimed here; instead, this forms the subject matter of the applicant's German Patent Application P35 14688.5 (D7237), submitted simultaneously [with this].
In particular, in the above mentioned Formula I, R can represent a straight chain or branched alkyl group with 3 to 19 carbon atoms, a cycloaliphatic residue with 3 to 6 ring hydrocarbon [sic] atoms, possibly substituted with alkyl groups and/or halogen atoms, a phenyl or naphthyl group possibly substituted with alkyl groups, alkoxy groups, fluorine or bromine atoms, and/or nitro groups, or a 5-or 6-membered heterocyclic group containing oxygen, sulfur or nitrogen atoms.
Suitable starting materials for the production of the 2,2-dibromo-3-oxonitriles of Formula I in accordance with the process stated in the preceding include, for example, esters of the following carboxylic acids: butyric acid, valerianic acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, pivalic acid, 2,2-dimethylbutyric acid, 2,2-dimethylvalerianic acid, 2-ethylhexanecarboxylic acid, cyclopropanecarboxylic acid, 1-methylcyclopropanecarboxylic acid, 2-ethylcyclopropanecarboxylic acid, cyclobutanecarboxylic acid, 2-methylcyclopropanecarboxylic acid, 3-propylcyclobutanecarboxylic acid, cyclopentanecarboxylic acid, 1-ethylcyclopentanecarboxylic acid, 2-methylcyclopentanecarboxylic acid, 3-propylcyclopentanecarboxylic acid, cyclohexanecarboxylic acid, 1-methylcyclohexylcarboxylic acid, 2-methylcyclohexanecarboxylic acid, 3,4-dimethylcyclohexanecarboxylic acid, 2,2-dichloro-1-methylcyclopropanecarboxylic acid, benzoic acid, 2-methylbenzoic acid, 3-methylbenzoic acid, 4-methylbenzoic acid, 2,4-dimethylbenzoic acid, 2-fluorobenzoic acid, 3-fluorobenzoic acid, 4-fluorobenzoic acid, 2-bromobenzoic acid, 3-bromobenzoic acid, 4-bromobenzoic acid, 2,4-dibromobenzoic acid, 2,5-dibromobenzoic acid, 2-methoxybenzoic acid, 2-ethoxybenzoic acid, 3-methoxybenzoic acid, 4-methoxybenzoic acid, 3,4-dimethoxybenzoic acid, 2-nitrobenzoic acid, 3-nitrobenzoic acid, 4-nitrobenzoic acid, 2,4-dinitrobenzoic acid, 2,5-dinitrobenzoic acid, 3,5-dinitrobenzoic acid, 2-trifluoromethylbenzoic acid, 4-trifluoromethylbenzoic acid, 1-naphthalenecarboxylic acid, 2-naphthalenecarboxylic acid, furan-2-carboxylic acid, furan-3-carboxylic acid, 5-bromo-2-methylfuran-3-carboxylic acid, tetrahydrofuran-2-carboxylic acid, thiophene-2-carboxylic acid, thiophene-3-carboxylic acid, 5-methylthiophene-2-carboxylic acid, tetrahydrothiophene-3-carboxylic acid, picolinic acid, nicotinic acid and isonicotinic acid.
The alcohol component of the carboxylic acid ester of the Formula II can consist of methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol and tert-butanol, wherein methyl esters are particularly preferred.
The first step of the above described process involves
REFERENCES:
Chem. Abstracts, Gault et al., vol. 61; 14523d, No. 12, (1964).
Mikolajczyk et al., Chem. Abstracts, vol. 83, No. 13; 113818e, (1975).
Methoden der Organischen Chemie, pp. 573-574 (1972).
Chem. Abstracts, Bodalski et al., vol. 84, No. 23, 164406x (1976).
Block, R., Chem. Abstracts, vol. 65; 18493g (1966).
Patents Abstracts of Japan, vol. 10, No. 172 (1986) 85 C 354.
Krause Horst-Juergen
Lehmann Rudolf
Leinen Hans-Theo
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Millson Jr. Henry E.
Richter J.
Schwartz Richard A.
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