Patent ID: 6562994
Filing Date: 2003-05-13
Classification: C07C,C07D

Abstract:
A process for the preparation of an N-(substituted phenyl)-3-alkyl-, aryl- or heteroarylsulfonyl-2-hydroxy-2-alkyl- or haloalkylpropanamide of formula I whereinY is cyano, nitro, perfluoroalkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl; R is perfluoroalkyl, cyano, nitro, alkylcarbonyl, alkoxycarbonyl, alkyl or alkoxy; R1 is alkyl or haloalkyl; and R2 is alkyl, aryl or heteroaryl, which process comprises:(a) reacting a substituted benzene of formula II (II) â€ƒwherein Y and R are as described above, X is F, Cl, Br, I or â€”OSO2R3, and R3 is alkyl or aryl with an &agr;,&bgr;-unsaturated propanamide of formula III â€ƒwherein R1 is as described above in the presence of a first base to form an N-(substituted phenyl)-&agr;,&bgr;-unsaturated propanamide of formula IV (b) reacting the formula IV propanamide with an epoxidizing agent to form an epoxide of formula V (c) reacting the formula V epoxide with a thiol of formula VI R2SHâ€ƒâ€ƒ(VI) â€ƒwherein R2 is as described above in the presence of a second base to form a sulfide of formula VII (d) reacting the formula VII sulfide with an oxidizing agent.