Water → BendaMustine IMpurity C

Participants

Reaction Conditions

Reaction Steps

4-{5-[Bis-(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl}-butyric acid isopropyl ester (5 g) and dichloromethane (50 mL) are charged into a round bottom flask and stirred at 28° C. Thionyl chloride (2.6 mL, 2.6 M) is slowly added at the same temperature and the reaction mass is allowed to settle for 30 minutes. The reaction mixture is heated to a temperature of 38-40° C. and the mixture is stirred for 90 minutes. Cooled the reaction mass to 25-30° C., dichloromethane layer (25 mL) and water (25 mL) are added and stirred. Separated the organic layer and washed with saturated sodium bicarbonate solution (25 mL) and saturated brine solution (25 mL). The organic layer is concentrated under vacuum at 45° C. to obtain 10-15 mL of the concentrated mass, cooled the mass to 25-30° C. N-heptane (62.5 mL) is added to the mass slowly at 28° C., stirred for about 1 hour, filtered and dried under vacuum to give 4-{5-[bis-(2-chloroethyl)amino]-1-methyl 1H-benzoimidazol-2-yl}-butyric acid isopropyl ester compound. Yield: 4.4 g.

Provenance & Evidence