Dimethylformamide → HCID 9813609, compound

Participants

Reaction Steps

A stirred mixture of 10 g (0.030 mole) of 3-bromo-2-phenyl-1,5-benzothiazepin-4(5H)-one from part A, 10 g (0.11 mole) of CuCN, and 75 ml of dimethylformamide is treated with 1 ml of pyridine, heated, and the resulting dark solution refluxed for 2 hours. After cooling, the reaction mixture is poured into a vigorously stirred mixture of 600 ml of ice-water, 600 ml of concentrated NH4OH, and 300 ml of CHCl3. Stirring is continued until essentially 2 clear layers are obtained. The layers are separated and the blue aqueous NH4OH layer is extracted with additional CHCl3 (4×150 ml). The combined organic layers are washed with 10% NH4OH (2×150 ml), then with 150 ml of H2O, dried (MgSO4), and the solvent evaporated (finally at 1 mm. pressure to remove dimethylformamide) to give 5.9 g of a reddish, partly solid residue. The latter is crystallized from 60 ml of MeCN to give 2.2 g (30%) of a pale yellow solid, m.p. 263°-265°(dec.).

Provenance & Evidence