METHOD OF SYNTHESIS OF SUBSTITUTED N-ALLYLDICHLOROACETANILIDES Russian patent published in 1995 - IPC

FIELD: organic chemistry. SUBSTANCE: product: N-allyldichloroacetanilides of the formula where M-N[C(O) CHCl₂]-CH₂-CH=CHR₃ where R₁-H, CH₃, CF₃, Cl, Br; R₂-H, CH₃, CF₃, Cl; R₃-H, CH₃,. The end product is synthesized by acylation of substituted anilines with dichloroacetic acid chloroanhydride followed by allylation of synthesized acetanilide derivative with allylhalogenide of the formula X-CH₂-CH=CHR₃, where X Cl, Br, J, and R₃ as indicated above. Process is carried out in aqueous-alkaline medium at 40-90 C in acetonitrile in the presence of catalyst of the formula R′R″R″′R″″N⁺Y^-, where R′, R″, R″′- (C₁-C₂₀)-alkyl; R″″-(C₂-C₂₀)-alkyl, cyclohexyl. In the case of use of catalysts showing symmetric structure the total content of carbon atoms in substituents is R^I-R^II≥ 12; Y Cl, Br, J. Catalyst concentration is 2-5 wt.-% of dichloroacetanilide. Synthesized compounds were used for herbicide synthesis of pyrrolidone order. EFFECT: increased yield, simplified process. 2 cl, 1 tbl