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

HRID 989274Notes

Reaction equation

HRID 989274 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 separated, dried over MgSO4, filtered and concentrated to afford compound 3 as a white solid.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-09a01a9c10b341459b9f20a5fd8a78cf
Source dataset
uspto-grants-2003_10
Patent number
US06638970B2

Reaction notes

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