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

HRID 2210987Notes

Reaction equation

HRID 2210987 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[Na+].[Na+].[Cl:16][CH2:17][C:18](Cl)=[O:19]>C1(C)C=CC=CC=1.O>[Cl:16][CH2:17][C:18]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9])=[O:19]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 68962,6-DimethylanilineHCID 10340Sodium Carbonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In 3 l of toluene was dissolved 182 g of 2,6-xylidine, and in 1.5 l of water was dissolved 159 g of sodium carbonate. The two solutions were combined, and 203 g of chloroacetyl chloride was added thereto dropwise over 1.5 hours at an inner temperature of from 20° to 35° C., followed by stirring at that temperature for 1.5 hours. The reaction mixture was cooled with ice, and the precipitated crystals were collected by filtration and dried under reduced pressure to obtain 282 g (95%) of the titled compound.

Workup

  1. temperatureThe reaction mixture was cooled with ice
  2. filtrationthe precipitated crystals were collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-298a83482ba448ce944d95efaaa7b011
Source dataset
uspto-grants-1995_10
Patent number
US05461157

Reaction notes

Loading…