GB716190A - Acrylonitriles and processes for making the same - Google Patents

Abstract

The invention comprises acrylonitriles of the general formula RO-CR1 = C(Ar)CN where Ar is phenyl or halophenyl, R is lower alkyl and R1 is hydrogen or lower alkyl. The compounds are prepared by treating an a -aryl-b -hydroxyacrylonitrile with an ortho ester, at a temperature not exceeding the boiling point of the ortho ester and under conditions such that the volatile products are continuously removed. The a -aryl-b -alkoxyacrylonitrile is recovered by distillation. In examples (1) a -p-chlorophenyl-b -ethoxyacrylonitrile is prepared by heating a -formyl-p-chlorophenylacetonitrile with ethyl orthoformate; (2) a - 2 : 4 - dichlorophenyl-b - methoxyacrylonitrile is made from a -formyl - 2 : 4 - dichlorophenylacetonitrile and methyl orthoacetate by heating together; (3) a - p - chlorophenyl - b - ethoxy - b - methylacrylonitrile from a - acetyl - p - chlorophenylacetonitrile and ethyl orthoformate; (4) a -31 : 41 - dichlorophenyl - b - methoxy - b -methylacrylonitrile from the corresponding ketonitrile and methyl orthoacetate; (5) a -(3 : 4 - dichlorophenyl) - b - ethoxy - b - methylacrylonitrile from a -acetyl-3 : 4-dichlorophenylacetonitrile and ethyl orthoformate; (6) a -m - chlorophenyl - b - n - butoxyacrylonitrile from a -formyl-m-chlorophenyl-acetonitrile and n - butyl orthoformate; (7) a - p - chlorophenyl - b - ethoxy - b - ethylacrylonitrile from a - propionyl - p - chlorophenylacetonitrile and ethyl orthoformate; (8) a - phenyl - b - ethoxy-b - ethylacrylonitrile from a - propiophenylacetonitrile and ethyl orthoformate; (9) a -p-tolyl - b - methoxy - b - methylacrylonitrile from a -acetyltolylacetonitrile and methyl orthoacetate; (10) a - p - chlorophenyl - b - methoxyacrylonitrile from a - formyl - p - chlorophenylacetonitrile and methyl orthopropionate; (11) a - p - chlorophenyl - b - ethoxy - b - n - heptylacrylonitrile from a - caprylyl - p - chlorophenylacetonitrile and ethyl orthoformate; (12) a - phenyl - b - n - amyloxy - b - methylacrylonitrile from a - acetylphenylacetonitrile and n - amyl orthoformate; (13) a - phenyl-b - n - propoxy - b - propylacrylonitrile from a -butyrylphenylacetonitrile and n - propyl orthoformate; (14) a - p - chlorophenyl - b -ethoxyacrylonitrile from a - formyl - p - chlorophenylacetonitrile and ethyl orthoacetate. When reacted with guanidine this gives 2 : 4-diamino - 5 - p - chlorophenylpyrimidine; (15) b - ethoxy - b - ethyl - a - p - chlorophenylacetonitrile from a - propionyl - p - chlorophenyl acetonitrile and ethyl orthoformate. With guanidine this compound reacts to form 2 : 4-diamino - 5 - p - chlorophenyl - 6 - ethylpyrimidine; (16) b - ethoxy - b - ethyl - a - p - chlorophenylacrylonitrile from a -propionyl-p-chlorophenylacetonitrile and ethyl orthopropionate. When reacted with guanidine this gives 2 : 4-diamino - 5 - p - chlorophenyl - 6 - ethylpyrimidine. Specification 715,813 is referred to