Chloroacetyl chloride → 2-Chloro-N-[2-(chloromethyl)-6-(trifluoromethyl)phenyl]acetamide

HRID 2290959Notes

Reaction equation

HRID 2290959 reaction equation
[Cl-].[Cl:2][CH2:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:5]=1[NH3+:6].[Cl:15][CH2:16][C:17](Cl)=[O:18]>C(Cl)CCl>[Cl:2][CH2:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[C:5]=1[NH:6][C:17](=[O:18])[CH2:16][Cl:15]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 201483412-(Chloromethyl)-6-(trifluoromethyl) anilinium chloride

Product 1

HCID 133914032-Chloro-N-[2-(chloromethyl)-6-(trifluoromethyl)phenyl]acetamideYield 93.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A slurry of 19.85 g (0.0947 mol) of 2-(chloromethyl)-6-(trifluoromethyl) anilinium chloride (prepared as in Example 1 from 20.0 g of sulfoxide) was refluxed in ethylene dichloride with 11.2 g (0.0991 mol) of chloroacetyl chloride for 30 minutes followed by addition of 1.0 g (0.0089 mol) of additional CAC and further reflux for 30 minutes. The virtually clear solution was then cooled to room temperature, washed with 10% aqueous sodium carbonate (80 ml) and dried using sodium sulfate. Evaporation and drying gave 22.14 g of white 2'-(chloromethyl)-6'-(trifluoromethyl)-2-chloroacetanilide assaying 93.5% for an overall yield from sulfoxide of 85.7%.

Workup

  1. additionfollowed by addition of 1.0 g (0.0089 mol) of additional CAC
  2. temperaturefurther reflux for 30 minutes
  3. washwashed with 10% aqueous sodium carbonate (80 ml)
  4. customdried
  5. customEvaporation
  6. customdrying

Sources & evidence

ORD record
ord-1790acb319884d61bd66fb5f891c576c
Source dataset
uspto-grants-1986_10
Patent number
US04618713

Reaction notes

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