Ammonia → 5-(2-Chlorophenyl)-1,3-dihydro-7-iodo-2H-thieno[2,3-e]-1,4-diazepin-2-one

Participants

Reaction Steps

A solution of 54.8 g of 5-(2-chlorophenyl)-1,3-dihydro-2H-thieno[2,3-e][4,1]diazepin-2-one [NL patent 7,205,730, Nov. 1972, Hoffmann-La Roche & Co., AG, Basle]in 350 ml of acetic acid and 350 ml of methanol was treated with 64.4 g of iodine monochloride and 16.2 g of sodium acetate. The mixture was stirred for 15 minutes at room temperature. A solution of 65 g of sodium bisulfite in 350 ml of water was then added and stirring was continued for 10 minutes. The mixture was neutralized by addition of 500 ml of conc. ammonia and 1 kg of ice. The precipitated product was filtered off and washed with water and ethanol. Recrystallization from tetrahydrofuran/ ethanol gave off-white crystals of the title compound with m.p. 229°-231°.

Provenance & Evidence