Nitrogen → HCID 20188514, compound

Participants

Reaction Steps

A stirred mixture of 7-chloro-1,3-dihydro-3-methyl-5-phenyl-2H-1,4 -benzodiazepine-2-thione (3.0 g, 0.01 mol), phenyl acetic acid hydrazide (4.95 g, 0.033 mol) and butanol (150 ml) was refluxed for 16 hours while N2 was being bubbled through the mixture. The reaction mixture was concentrated under high vacuum, and the residue mixed with iced H2O. The product was filtered and dissolved in CH2Cl2. The CH2Cl2 was washed with dilute HCl and brine, dried over Na2SO4 and concentrated in vacuo. At this point it appeared that complete cyclization had not been achieved. Therefore, the residue was combined with acetic acid (100 ml) and refluxed for 2 hours under N2. The reaction mixture was concentrated in vacuo and the residue mixed with CH2Cl2 and H2O. The CH2Cl2 was washed with NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. The material was crystallized from EtOAc-Skelly B to give 1.55 g, mp 195°-197° of the subtitled intermediate, which had a C:H:N:Cl ratio of 72.38:4.85:14.16:8.81. Calculated for C24H19N4Cl: 72.26:4.80:14.05:8.89.

Provenance & Evidence