Sodium hydride → HCID 18940562, compound

HRID 356146Notes

Reaction equation

HRID 356146 reaction equation
[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]([CH3:19])[CH2:10][C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1>O>[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]([CH3:19])[CH:10]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[C:9]1=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 18940576HCID 18940576, compound

Product 1

HCID 18940562HCID 18940562, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-benzyl-4-methyl-1,3-dihydro-1,5-benzodiazepin-2(2H)-one (3.0 g, 13.1 mmol) in N-dimethylformamide (20 mL) was added sodium hydride (content 60%, 0.51 g, 12.8 mmol). The mixture was stirred for 15 minutes, to which was added 4-methoxybenzylbromide (2.3 g, 11.5 mmol), and the mixture was stirred for further 30 minutes. The reaction mixture was diluted with water, which was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The concentrate was crystallized from ethyl acetate-hexane to give 3.3 g of the titled compound. Yield 76%. m.p. 136°-137° C.

Workup

  1. stirringthe mixture was stirred for further 30 minutes
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe concentrate was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7f920472dc8a434e953f3773b9ee6c48
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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