Acetyl chloride → Acetamide, N-ethyl-N-(4-nitrophenyl)-

HRID 1356994Notes

Reaction equation

HRID 1356994 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2].[C:13](Cl)(=[O:15])[CH3:14]>C1C=CC=CC=1>[C:13]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 19318N-Ethyl-p-nitroaniline

Product 1

HCID 74583Acetamide, N-ethyl-N-(4-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of N-ethyl 4-nitroaniline (1.5 g, 9.026 mmol) in benzene (15 ml), is added acetylchloride (10 ml) and the mixture refluxed for 40 minutes. The solvent is removed by evaporation. The residue is dissolved in ethyl acetate prior to washing with 2N sodium bicarbonate and water, drying (MgSO4) and evaporation. The product is dried under vacuum; ES+ (M+1) 208.57.

Workup

  1. temperaturethe mixture refluxed for 40 minutes
  2. customThe solvent is removed by evaporation
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washto washing with 2N sodium bicarbonate and water
  5. customdrying
  6. custom(MgSO4) and evaporation
  7. customThe product is dried under vacuum

Sources & evidence

ORD record
ord-a467fa6e925242a88b7ed78699b8dc79
Source dataset
uspto-grants-2003_07
Patent number
US06589950B1

Reaction notes

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