Chloroacetyl chloride → 2-chloro-N-(2-fluoro-4-nitrophenyl)-N-methylacetamide

HRID 2114871Notes

Reaction equation

HRID 2114871 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[F:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[NH:16][CH3:17]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:16]([C:8]1[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=1[F:6])[CH3:17])=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 119518472-fluoro-N-methyl-4-nitroaniline

Product 1

HCID 119518482-chloro-N-(2-fluoro-4-nitrophenyl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Chloroacetyl chloride (1.87 ml, 0.0235 mol) is added to (2-fluoro-4-nitro-phenyl)-methyl-amine (14, 2.00 g, 0.0118 mol) in toluene (20 ml) and the mixture refluxed for 3 hours. The mixture is evaporated under vacuum and the residue triturated with ethanol to give the title compound as a white solid. HPLC r.t. 4.57 min; MS for C9H8ClFN2O3 m/z 247 (M+H)+.

Workup

  1. temperaturethe mixture refluxed for 3 hours
  2. customThe mixture is evaporated under vacuum
  3. customthe residue triturated with ethanol

Sources & evidence

ORD record
ord-d04273549bfb4216a8f25c238b15d52e
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

Loading…