Chloroacetyl chloride → 2-Chloro-N-(2,6-dimethylphenyl)acetamide

HRID 2210988Notes

Reaction equation

HRID 2210988 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].[OH-].[Na+].[Cl:12][CH2:13][C:14](Cl)=[O:15]>ClC=CCl>[Cl:12][CH2:13][C:14]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9])=[O:15]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 68962,6-DimethylanilineHCID 14798Sodium Hydroxide

Product 1

HCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 109001,2-DichloroethyleneSolvent

Procedure

In 4 l of 1,2-dichloroethylene was dissolved 182 g of 2,6-xylidine, and 1.6 l of a 1N sodium hydroxide aqueous solution was added thereto, followed by stirring. To the mixture was added dropwise 203 g of chloroacetyl chloride over 1.5 hours at an inner temperature between 20 and 35° C. The mixture was stirred at that temperature for 1.5 hours. The reaction mixture was separated into two layers, and the organic layer was concentrated under reduced pressure. The precipitate was collected by filtration and dried under reduced pressure to obtain 282 g (95%) of the titled compound.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at that temperature for 1.5 hours
  3. customThe reaction mixture was separated into two layers
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. filtrationThe precipitate was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-c166de2d58db4e6ea14478b98cb28a6d
Source dataset
uspto-grants-1995_10
Patent number
US05461157

Reaction notes

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