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

HRID 1838933Notes

Reaction equation

HRID 1838933 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C([O-])(O)=O.[Na+].[Cl:15][CH2:16][C:17](Cl)=[O:18]>CCOCC>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:17](=[O:18])[CH2:16][Cl:15]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 68962,6-DimethylanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2,6-dimethylaniline (9.8 g, 81.2 mmol) was dissolved in ether (100 mL) and saturated aqueous NaHCO3 (100 mL) and the reaction mixture was cooled in an ice/water bath. To the cold solution was added chloroacetyl chloride 2 (9.17 g, 81.2 mmol) dropwise over a period of 2 h. The mixture was allowed to warm to RT over 14 h. The mixture was diluted with 100 mL ether and the organic layer was dried over MgSO4, filtered and concentrated to afford compound 3 as a white solid.

Workup

  1. dry with materialthe organic layer was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9209ccba721e43d5827cda59166d1165
Source dataset
uspto-grants-2004_01
Patent number
US06677343B2

Reaction notes

Loading…