Dimethylformamide → 5-Methoxy-1-methyl-7-nitro-5-phenyl-1,5-dihydro-2H-1,4-benzodiazepin-2-one

HRID 441486Notes

Reaction equation

[CH3:1][O:2][C:3]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=2[NH:7][C:6](=[O:17])[CH:5]=[N:4]1.[CH3:24]N(C)C=O.[H-].[Na+].CI>C(OCC)C.O>[CH3:1][O:2][C:3]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:9]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]([CH3:24])[C:6](=[O:17])[CH:5]=[N:4]1

Participants

Conditions

Temperature: -30 °C

Procedure

To a mixture of 5-methoxy-7-nitro-5-phenyl-1,5-dihydro-2H-1,4-benzodiazepin-2-one (920 mg) and dry dimethylformamide (8 ml), sodium hydride (50% suspension in a mineral oil; 156 mg) is added under cooling at -30° C. for 15 minutes. Methyl iodide (842 mg) is added to the mixture, which is stirred at room temperature for 10 minutes. The reaction mixture is poured into icy water, and shaken with diethyl ether. The organic layer is dried over sodium sulfate and evaporated to remove the solvent. The residue is recrystallized from methylene chloride/isopropyl ether to give 5-methoxy-1methyl-7-nitro-5-phenyl-1,5-dihydro-2H-1,4-benzodiazepin-2-one (708 mg) as fine prisms melting at 163 to 164° C.

Workup

addition156 mg) is added
dry with materialThe organic layer is dried over sodium sulfate
customevaporated
customto remove the solvent
customThe residue is recrystallized from methylene chloride/isopropyl ether

Sources & evidence

ORD record: ord-dce874a2d87f481f8973d5586ec5a8b1
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04041026

Reaction notes

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