3,4-Dichlorobenzaldehyde → (E)-9-chloro-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine dihydrochloride

Participants

Reaction Steps

To a solution of 91 mg (0.275 mmol) of (9-chloro-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester in 2 ml of tetrahydrofuran was added 19 mg (0.48 mmol) of sodium hydride (60% dispersion in mineral oil). After 10 minutes 50 mg (0.29 mmol) of 3,4-dichlorobenzaldehyde was added and the mixture was stirred for 18 hours. The product was purified by column chromatography (20 g IST pre-packed column) eluting with 1% methanol/dichloromethane and treated with 0.10 ml of 4M hydrogen chloride in dioxan. The solvent was evaporated to give 90 mg of (E)-9-chloro-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine dihydrochloride as an orange solid; MS: m/e 352.7 [M+H]+.

Provenance & Evidence