Benzyl Bromide → HCID 18940592, compound

HRID 356145Notes

Reaction equation

HRID 356145 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH2:9][C:8](=[O:10])[NH:7][C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[N:4]=1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.O>[CH2:19]([N:7]1[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[N:4]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:9]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]1=[O:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5357162070-87-3

Product 1

HCID 18940592HCID 18940592, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-trifluoromethyl-1,3-dihydro-1,5-benzodiazepin-2(2H)-one(3.0 g, 13.1 mmol) in N,N-dimethylformamide(20 mL) was added sodium hydride (content 60%, 1.1 g, 27.5 mmol), and the mixture was stirred for 15 minutes. To the mixture was added benzyl bromide (4.7 g, 27.5 mmol), which 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 61%. m.p. 150°-151° C.

Workup

  1. stirringwas 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-fd33974249bc46cca45587119625ffa6
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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