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

HRID 1838800Notes

Reaction equation

HRID 1838800 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 EtherSolvent

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 extracted with EtOAc (3×50). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was triturated in ether and filtered to afford compound 3 as a white solid.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×50)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated in ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-58598dec7fb94c069e051c03039d14f1
Source dataset
uspto-grants-2004_01
Patent number
US06677336B2

Reaction notes

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