Acetyl chloride → N-[1-(4-Chloro-3-nitrophenyl)ethyl]acetamide

HRID 1410188Notes

Reaction equation

HRID 1410188 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][NH:11]C)=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16].[C:18]([O-])(O)=O.[Na+]>C1COCC1>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([CH:10]([NH:11][C:1](=[O:3])[CH3:2])[CH3:18])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 516892Sodium BicarbonateHCID 28338349Benzenemethanamine, 4-chloro-N-methyl-3-nitro-

Product 1

HCID 59529853N-[1-(4-Chloro-3-nitrophenyl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TEA (0.28 mL, 2.0 mmol) followed by acetylchloride (96 L, 1.3 mmol) were added to 4-chloro-methyl-3-nitrobenzylamine (0.27 g, 1.3 mmol) in THF (5 mL) at rt. The mixture was stirred at rt for 3.5 h and additional acetylchloride (20 L, 0.27 mmol) was added. After 1 h at rt, NaHCO3 (aq, 5%) was added and the mixture extracted with EtOAc.

Workup

  1. waitAfter 1 h at rt
  2. extractionthe mixture extracted with EtOAc

Sources & evidence

ORD record
ord-ac1fbc65b43048e3a3db36cd371872de
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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