Ammonia → 6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-carboamide
Reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17](Cl)=[O:18])=[CH:16][C:3]1=2.[NH3:20]>O1CCCC1>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([C:17]([NH2:20])=[O:18])=[CH:16][C:3]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The remaining half of the acid chloride IV was added to a mixture of 150 ml of concentrated ammonia and 150 ml of tetrahydrofuran. Then, the mixture was stirred at room temperature for three hours and concentrated under reduced pressure. The residue was vigorously stirred together with 300 ml of saturated aqueous solution of sodium bicarbonate and 100 ml of ether, and the solid was collected by filtration and dried to obtain 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-carboamide VIII in a quantitative yield. Recrystallization from methanol gave pure crystals having a melting point of 227°-228° C. IR spectrum (KBr tablet, cm-1): 3430, 3150, 1680, 1635, 1600, 1370.