[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:18]=[CH:17][S:16][C:10]=2[NH:11][C:12](=[O:15])[CH2:13][N:14]=1.[I:19]Cl.C([O-])(=O)C.[Na+].S(=O)(O)[O-].[Na+].N>O.CO.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:18]=[C:17]([I:19])[S:16][C:10]=2[NH:11][C:12](=[O:15])[CH2:13][N:14]=1A 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°.
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