Methanol → N'-(4-((2-chloro-6-methyl-4-pyrimidinyl)oxy)-phenyl)-N,N-dimethylurea

Participants

Reaction Steps

4-Hydroxyphenyl-N,n-dimethylurea (14.4 grams; 0.08 mole) was mixed with a solution of sodium methylate (prepared by mixing sodium metal (1.84 grams) in 50 milliliters (ml) of methanol) and the resulting sodium 4-hydroxyphenyl-N,N-dimethylurea solution added gradually over a period of about one hour to a solution of 2,4-dichloro-6-methylpyrimidine (13.04 grams; 0.08 mole) in 70 ml. of dimethylsulfoxide. During the addition, the reaction temperature rose from about 52°C. to a temperature from between about 60° to about 65°C. The resulting reaction mixture was maintained at temperatures from between about 60° to about 70°C. for a period of about 80 minutes. Following the reaction period, the reaction mixture was poured into about 400 ml. of cold water and the resulting tan product precipitate recovered by filtration and washed with additional portions of water. The product precipitate was dissolved in boiling benzene and the resulting solution treated with activated charcoal. Approximately one-half of the solvent was removed by evaporation and the remaining portion was cooled to crystallize the product. As a result of these operations, the desired title product was obtained as a light tan crystalline solid having a melting point of 176°-178°C.

Provenance & Evidence