Chloroacetyl chloride → 2-Chloro-N-methyl-N-(4-nitro-phenyl)-acetamide

HRID 1887714Notes

Reaction equation

HRID 1887714 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[OH-].[K+]>CCOC(C)=O.O>[Cl:1][CH2:2][C:3]([N:7]([CH3:6])[C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)=[O:4]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 7483N-Methyl-4-nitroanilineHCID 14797Potassium Hydroxide

Product 1

HCID 114361292-Chloro-N-methyl-N-(4-nitro-phenyl)-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Chloroacetyl chloride (1.05 mL, 13.1 mmol) is added in one portion to a biphasic mixture of N-methyl-4-nitroaniline (1.0 g, 6.57 mmol), KOH (1.11 g, 19.7 mmol) in 12 mL EtOAc and 12 mL H2O, cooled to 0° C. The resulting mixture is stirred at this temperature for 5 min, then the ice bath was removed and it was allowed to warm to RT. The reaction was stirred for an additional one hour at RT.

Workup

  1. customthe ice bath was removed
  2. temperatureto warm to RT
  3. stirringThe reaction was stirred for an additional one hour at RT

Sources & evidence

ORD record
ord-7ea943c4ff404856983585c5322e5957
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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