Sodium hydride → HCID 53855886, compound

HRID 865925Notes

Reaction equation

HRID 865925 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:5]=1.Br[CH2:28][C:29]([N:31]([CH3:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>CN(C=O)C>[CH3:3][C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:28][C:29]([N:31]([CH3:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:30])[C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 34495Acetanilide, 2-bromo-N-methyl-HCID 135744107HCID 135744107, compound

Product 1

HCID 53855886HCID 53855886, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

80% Sodium hydride in oil (102 mg) was added to a solution of phenylmethyl [2,3-dihydro-5-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]carbamate (1.00 g) in dry DMF (10 ml) under nitrogen. The mixture was stirred for 0.5 h at 23° and was treated with a solution of 2-bromo-N-methyl-N-phenylacetamide (707 mg) in dry DMF (1 ml). The mixture was stirred at 23° for 1 h, partitioned between phosphate buffer solution (pH6.5) and EA, the organic phase was washed with water and dried. The solvent was evaporated in vacuo and the residue was purified by chromatography on alumina. Elution with MeOH-DCM (1:50) gave the title compound (568 mg).

Workup

  1. stirringThe mixture was stirred at 23° for 1 h
  2. custompartitioned between phosphate buffer solution (pH6.5) and EA
  3. washthe organic phase was washed with water
  4. customdried
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by chromatography on alumina
  7. washElution with MeOH-DCM (1:50)

Sources & evidence

ORD record
ord-df6a8fce052d47c18f89938a28d045c4
Source dataset
uspto-grants-1996_10
Patent number
US05569654

Reaction notes

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