Ethylene Glycol → Bosentan

Participants

Reaction Conditions

Reaction Steps

A mixture of sodium hydroxide (2.66 g), ethylene glycol (60 mL), tetrabutylammonium bromide (1 g) and 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2,2′-bipyrimidin-4-yl]benzenesulfonamide (10 g) was heated to 95° C. to 100° C. and the reaction mixture was stirred for 4 hours at 95° C. to 100° C. The mixture was cooled to 25° C. followed by the addition of dichloromethane (40 mL) and de-ionized water (180 mL). The pH of the reaction mixture was adjusted to 2 to 3 with concentrated hydrochloric acid. The reaction mixture was stirred for 10 minutes and the organic layer was separated. The aqueous layer was extracted with dichloromethane (10 mL). Both the organic layers were combined and washed with de-ionized water (50 mL). The dichloromethane was recovered under vacuum at 40° C. to 50° C. to obtain the title compound.

Provenance & Evidence