Water → HCID 14951370, compound

Participants

Reaction Conditions

Reaction Steps

To an ambient solution of N-[2-[5-(methylsulfonyl)-1,3,4-oxadiazol-2-yl]phenyl]-3-trifluoromethyl benzenamine (210.4 mg, 0.549 mmoles) in 5 ml of dimethylformamide is added 1 ml of water followed by cyanamide (196.0 mg, 4.66 mmoles) and triethylamine (100 μl, 0.717 mmoles). The reaction mixture is stirred at 80° C. overnight. An additional amount of cyanamide (96 mg) is added, and heating is continued for six hours. The mixture is poured into ether and extracted into 0.3N sodium hydroxide. The aqueous layer is acidified with 1N hydrochloric acid, and the resulting white solid is collected by filtration, washing with water. Recrystallization from acetonitrile provides 95.8 mg (51%) of 5-[2-[[3-(trifluoromethyl)phenyl]amino]phenyl]-1,3,4-oxadiazol-2-yl-cyanamide, mp above 230° C.

Provenance & Evidence