4-Isothiocyanato-N,N-dimethyl-1-naphthalenamine → N-(7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-[4-(dimethylamino)-1-naphthalenyl]-thiourea

Participants

Reaction Steps

To a solution of 3-amino-7-chloro-5-phenyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (INTERMEDIATE 1) (0.299 g, 1 mmol) in dichloroethane (15 mi) was added 4-isothiocyanato-N,N-dimethyl-1-naphthalenamine (0.230 g, 1 mmol). The reaction mixture was stirred at room temperature for 17 hours. The solvent was evaporated in vacuo, the residue was triturated with ether and the title compound was obtained as a colorless solid (0.345 g, 65%). 1H-NMR (CD3OD): δ 8.25 (d, 8.4 Hz, 2H), 8.00 (d, J=8.4 Hz, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.85-7.81 (m, 2H), 7.77-7.72 (m, 2H), 7.65 (d, J=8.8 Hz, 1H), 7.61-7.58 (m, 4H), 7.51-7.47 (m, 2H), 7.29 (d, J=2.4 Hz, 1H), 6.01 (s, 1H) and 3.49 (s, 9H). MS (ESI) (M+H)+=528.

Provenance & Evidence