4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-carboxy-2-methoxyphenyl)-N-propylamino]thiazole → 4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-hydroxymethyl-2-methoxyphenyl)-N-propylamino]thiazole

Participants

Reaction Steps

At 0° C., under an inert atmosphere, 1.5 g of 4-(2-chloro-4-methoxyphenyl)-5methyl-2-[N-(5-carboxy-2-methoxyphenyl)-N-propylamino]thiazole are dissolved in 11 ml of tetrahydrofuran. 5 ml of a 1 M solution of lithium aluminium hydride in tetrahydrofuran are added slowly so that the temperature of the mixture does not exceed 10° C. After 2 hours at room temperature, the reaction mixture is cooled with the aid of an ice bath and then hydrolyzed slowly. The crude material is alkalanized before being filtered over sodium sulphate. After evaporation under vacuum, the product is obtained by purification on a silica gel; eluent: dichloro-methane/ethyl acetate 95/5 (v/v); yield=87%. The expected product is in the form of a powder; m.p.=115° C.

Provenance & Evidence