Benzaldehyde → HCID 18940547, compound

HRID 356177Notes

Reaction equation

HRID 356177 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+].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O.O>[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11](/[CH:19]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10][C:9]1=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 24758Sodium hydrideHCID 18940576HCID 18940576, compound

Product 1

HCID 18940547HCID 18940547, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzyl-4-methyl-1,3-dihydro-1,5-benzodiazepin-2(2H)-one (3.0 g, 11.4 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (content 60%, 0.51 g, 12.8 mmol), and the mixture was stirred for 15 minutes at room temperature. To the reaction mixture was added benzaldehyde (1.45 g, 13.7 mmol), which was stirred for further 30 minutes at the same temperature. The reaction mixture was diluted with water, which was subjected to extraction with ethyl acetate. The extract solution was washed with water and dried, followed by concentration. The concentrate was crystallized from ethylacetate-hexane to give 1.9 g of the titled compound. Yield 75%. m.p. 150°-151° C.

Workup

  1. stirringwas stirred for further 30 minutes at the same temperature
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe extract solution was washed with water
  4. customdried
  5. concentrationfollowed by concentration
  6. customThe concentrate was crystallized from ethylacetate-hexane

Sources & evidence

ORD record
ord-ca89c9b630044eceb303dabf12d23ec9
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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