Methanesulfonic Acid → N-[2-(N,N-dimethylsulfamoyl)-phenylsulfonyl]-N'-(4-chloromethyl-6-methoxypyrimidin-2-yl)-urea

Participants

Reaction Steps

26.4 g of 2-(N,N-dimethylsulfamoyl)-benzenesulfonamide (0.1 mol) are suspended in 100 ml of acetonitrile; 15.7 g of 1,8-diazabicyclo(5,4,0)undec-7-ene DBU (0.1 mol) are added, and the mixture is stirred for 1 hour at room temperature. There are then added 21.4 g of diphenyl carbonate (0.1 mol) and stirring is continued for 1 hour. After a standing time of 15 hours, 9.7 g of methanesulfonic acid (0.1 mol) are added dropwise in the cold state. There are afterwards added 17.3 g of 2-amino-4-chloromethyl-6-methoxypyrimidine (0.1 mol), and the suspension is refluxed for 1 hour, in the course of which there is firstly formed a solution from which, after a short time, the product precipitates in crystalline form. The reaction mixture is cooled and the product is filtered off under suction to thus obtain 32 g of slightly yellowish product; m.p. 214°-216° C. (decomp.); yield 70% of theory.

Provenance & Evidence