Sodium hydride → HCID 69690118, compound

HRID 1276861Notes

Reaction equation

HRID 1276861 reaction equation
[H-].[Na+].[C:3]([NH:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:7])[CH2:4][CH2:5][CH3:6].[Br:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br>CN(C)C=O>[Br:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][CH2:6][CH2:5][CH2:4][C:3]([NH:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromideHCID 18315414HCID 18315414, compound

Product 1

HCID 69690118HCID 69690118, compoundYield 136.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

One-hundred milligrams of sodium hydride (60% water-in-oil suspension) were added to a solution of 247 mg of ethyl 3-butyrylamino-4-nitrobenzoate in 10 ml of N,N-dimethylformamide in a nitrogen atmosphere at room temperature in some divided portions. The reaction suspension was stirred at the same temperature for 1 hour, and a solution of 244 mg of 2-bromobenzyl bromide in 2 ml of N,N-dimethylformamide was gradually added dropwise thereto over a period of 10 minutes. The reaction mixture was stirred at room temperature for 1 hour, and was poured in ice water. The oily substance precipitated was extracted with methylene chloride. The organic solvent layer was washed with water, dried, and then concentrated under reduced pressure. The residue was developed through silica-gel flash column chromatography, and was eluted with a mixture of 25% ethyl acetate and n-hexane to give 540 mg of yellow oil of ethyl 3-[N-(2-bromobenzyl)butyrylamino-4-nitrobenzoate.

Workup

  1. waitover a period of 10 minutes
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. customThe oily substance precipitated
  4. extractionwas extracted with methylene chloride
  5. washThe organic solvent layer was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. washwas eluted with a mixture of 25% ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-322dc9c0d7924239bb2efb9e92917e98
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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