Ethanol → 7-Chloro-5-(2'-chloro-phenyl)-1,3-dihydro-3-(dimethylaminomethylene)-2H-1,4-benzodiazepin-2-one

HRID 1076389Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1.C(O)C.C(O[CH:27](OCC)[N:28]([CH3:30])[CH3:29])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C:9](=[CH:27][N:28]([CH3:30])[CH3:29])[N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 17925Delorazepam

HCID 70913Dimethylformamide diethylacetal

Product 1

HCID 1363535337-Chloro-5-(2'-chloro-phenyl)-1,3-dihydro-3-(dimethylaminomethylene)-2H-1,4-benzodiazepin-2-one

Conditions

Temperature: 130 °C

Procedure

A suspension of 50 gm of 7-chloro-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one in 100 ml of N,N-dimethyl-formamide diethylacetal was heated to 130°C in a vessel equipped with a descending condenser, whereby a clear solution was formed after a short time. The temperature of the reaction solution was maintained at 130°C for 40 minutes, during which time the ethanol formed by the reaction slowly distilled over. Thereafter, the reaction solution was allowed to cool, and the red precipitate was collected by vacuum filtration, washed with petroleum ether and recrystallized from methanol, whereupon it had a melting point of 239°-241°C. It was identified to be the compound of the formula ##SPC6##

Workup

customequipped with a descending condenser
customwhereby a clear solution was formed after a short time
customformed by the reaction
distillationslowly distilled over
temperatureto cool
filtrationthe red precipitate was collected by vacuum filtration
washwashed with petroleum ether
customrecrystallized from methanol, whereupon it

Sources & evidence

ORD record: ord-7f87dbed62cc469cb7913123ec3770ae
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03956492

Reaction notes

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