3,4-Dichlorobenzaldehyde → (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-8-(3-thienyl)-1H-1,4-benzodiazepine dihydrochloride

Participants

Reaction Steps

To 105 mg (0.27 mmol) of (1-methyl-8-thiophen-3-yl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester in 2 ml of tetrahydrofuran was added 19 mg (0.47 mmol) of sodium hydride (60% dispersion in mineral oil). After 10 minutes 49 mg (0.28 mmol) of 3,4-dichlorobenzaldehyde was added and the mixture was stirred for 3 hours. The product was purified by column chromatography (20 g IST pre-packed column) eluting with 1% methanol/dichloromethane and treated with 0.15 ml of 4M hydrogen chloride in dioxan. The solvent was evaporated and the residue was recrystallized from acetone to give 75 mg of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-8-(3-thienyl)-1H-1,4-benzodiazepine dihydrochloride as an orange solid; MS: 412 (M+).

Provenance & Evidence