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US 4,225,723 AGranted
Process for the preparation of substituted arylcyanoalkyl and diaryl cyanoalkylimidazoles
AssigneeRohm and Haas Company
InventorsGeorge A. Miller, Hak-Foon Chan, Harold E. Carley
Life of this patent
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Abstract
This invention relates to a process for the preparation of substituted arylcyanoalkyl and diarylcyanoalkylimidazoles, their acid addition salts and their metal salt complexes. These compounds are useful as broad spectrum protectant-eradicant fungicides.
Claims13
A process for the preparation of a compound of the formula:
- ##STR31## wherein Z is (C.sub.6 -C.sub.10) aryl or (C.sub.6 -C.sub.10) aryl substituted with up to 3 substituents independently selected from the group consisting of fluoro, chloro, bromo, iodo, nitro, cyano, methoxy, ethoxy, methyl, ethyl, propyl, butyl, trihalomethyl, phenyl and benzoyl;
- R.sup.1 is (C.sub.1 -C.sub.20) alkyl, (C.sub.3 -C.sub.8) cycloalkyl, (C.sub.3 -C.sub.8) alkenyl, (C.sub.5 -C.sub.8) cycloalkenyl, (C.sub.3 -C.sub.6) alkynyl, phenyl, benzyl or phenethyl or phenyl, benzyl or phenethyl substituted with up to three substituents independently selected from the group consisting of fluoro, chloro, bromo, iodo, nitro, cyano, methoxy, ethoxy, methyl, ethyl and trihalomethyl;
- R.sup.2 and R.sup.3 are independently hydrogen, (C.sub.1 -C.sub.20) alkyl, phenyl, benzyl or phenethyl or phenyl, benzyl or phenethyl substituted with up to three substituents independently selected from the group consisting of fluoro, chloro, bromo, iodo, nitro, cyano, methoxy, ethoxy, methyl, ethyl and trihalomethyl, or when taken together form (C.sub.4 -C.sub.8) cycloalkyl;
- R.sup.1 and Z when taken together form the group ##STR32## a is 0 to 5;
- b is 0 to 5;
- X is halogen;
- and c is 0 to 2, which comprises reacting
- (I) a molar equivalent of a benzylcyanide of the formula
- Z--CHR.sup.1 CN
- wherein Z and R.sup.1 are as defined above, and
- (II) about a molar equivalent amount of a dihaloalkane of the formula ##STR33## wherein R.sup.2, R.sup.3, a and b are as defined above and Hal is chlorine, bromine or iodine in the presence of
- (1) about a molar equivalent amount of sodium hydride;
- (2) about a molar equivalent amount of a 50% solution of NaOH;
- or
- (3) a catalytic amount of a quaternary ammonium halide catalyst of the formula ##STR34## wherein R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently (C.sub.1 -C.sub.4) alkyl and Hal is as defined above;
- either neat or in an inert solvent, at temperatures from about 20.degree. C. to about 160.degree. C. to form a arylcyanoalkyl halide of the formula ##STR35## then reacting a molar equivalent of said arylcyanoalkylhalide and (III) about a molar equivalent of an imidazole or an alkali metal salt thereof having the formula ##STR36## wherein Q is hydrogen, sodium, potassium or lithium, in the presence of (1), (2) or (3) above.
13 more elements
A process for the preparation of a compound of the formula ##STR38## which comprises:
- (1) reacting a molar equivalent of benzyl cyanide and about a molar equivalent of 1-chlorobutane in the presence of from about 0.01 to about 10% by weight (based on the benzyl cyanide) of tetrabutylammonium bromide and about a molar equivalent of a 50% aqueous NaOH solution (based on the molar equivalents of 1-chlorobutane) at temperatures from about 20.degree. C. to about 160.degree. C. in an inert solvent and isolating the 2-phenyl-hexanenitrile;
- (2) reacting a molar equivalent of said 2-phenylhexanenitrile and about a molar equivalent of dichloromethane in the presence of from about 0.01 to about 10% by weight (based on the 2-phenylhexanenitrile) of tetrabutylammonium bromide and about a molar equivalent of a 50% aqueous NaOH solution (based on the molar equivalent of dichloromethane) at temperatures from about 20.degree. C. to about 160.degree. C. in an inert solvent and isolating the 1-chloro-2-cyano-2-phenylhexane;
- (3) reacting a molar equivalent of said 1-chloro-2-cyano-2-phenylhexane and about a molar equivalent of imidazole, sodium salt at temperatures from about 20.degree. C. to about 160.degree. C. in an inert solvent and isolating the .alpha.-butyl-.alpha.-phenyl-1H-imidazole-1-propanitrile.
A process for the preparation of a compound of the formula ##STR39## which comprises:
- (1) reacting a molar equivalent amount of benzylcyanide, about a molar equivalent amount of 1-chlorobutane and about a molar equivalent amount of a 50% aqueous solution of NaOH at from about room temperature to about 50.degree. C.;
- (2) then adding to this reaction mixture about a molar equivalent amount of dibromomethane and isolating the 1-chloro-2-cyano-2-phenylhexane;
- (3) then reacting a molar equivalent amount of said 1-chloro-2-cyano-2-phenylhexane and imidazole either neat or with a high boiling solvent at temperatures from about 50.degree. C. to about 180.degree. C. and isolating the .alpha.-butyl-.alpha.-phenyl-1H-imidazole-1-propanitrile.
Dependencies are inferred from the claim text.