Water → 7-Chloro-5-methoxy-1-methyl-5-phenyl-1,5-dihydro-2H-1,4-benzodiazepin-2-one

HRID 441484Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH3:14])[C:12](=[O:15])[CH2:11][N:10]([N+]([O-])=O)[C:9]([O:25][CH3:26])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:8]=2[CH:27]=1.O.C(OCC)C>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH3:14])[C:12](=[O:15])[CH:11]=[N:10][C:9]([O:25][CH3:26])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:8]=2[CH:27]=1

Participants

Conditions

Temperature: -30 °C

Procedure

To a solution of sodium hydride (50% suspension in a mineral oil; 200 mg) in dry dimethylformamide (7.5 ml), 7-chloro-5-methoxy-1-methyl-4-nitro-5phenyl-1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one (500 mg) is added under cooling at -30° C. and with stirring, and the resultant mixture is stirred at -10° C. for 30 minutes. The reaction mixture is poured into icy water and shaken with diethyl ether. The organic layer is washed with water, dried over sodium sulfate, and evaporated to remove the solvent. The residue is crystallized from diethyl ether to give 7-chloro-5-methoxy-1-methyl-5-phenyl-1,5-dihydro-2H-1,4-benzodiazepin-2-one (192 mg) as colorless prisms melting at 146.5 to 147° C.

Workup

washThe organic layer is washed with water
dry with materialdried over sodium sulfate
customevaporated
customto remove the solvent
customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record: ord-1fa956f0e8874173a58464b7d99a8d6b
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04041026

Reaction notes

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