Chloroacetyl chloride → N-(4-(2-chloroacetyl)-3,5-dimethylphenyl)acetamide

HRID 1484705Notes

Reaction equation

HRID 1484705 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[Cl:13][CH2:14][C:15]([C:7]1[C:6]([CH3:8])=[CH:5][C:4]([NH:9][C:10](=[O:12])[CH3:11])=[CH:3][C:2]=1[CH3:1])=[O:16]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 74903Acetamide, N-(3,5-dimethylphenyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 118006191N-(4-(2-chloroacetyl)-3,5-dimethylphenyl)acetamideYield 57.9%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

To a solution of N-(3,5-dimethylphenyl)acetamide (4.0 g, 24.5 mmol) and ClCH2COCl (4.2 g, 37 mmol) in CS2 (30 mL), AlCl3 (10.0 g, 74.9 mmol) was added in portions. The resulting mixture was refluxed overnight. The reaction mixture was then cooled down to room temperature before the CS2 layer was decanted. The resulting complex was decomposed by pouring onto a mixture of ice (500 g) and concentrated HCl (30 mL). The solid was collected by suction, washed with 1N HCl and water, and recrystallized in EtOH to afford N-(4-(2-chloroacetyl)-3,5-dimethylphenyl)acetamide as a brown powder (3.4 g, 57.9%), which was used without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. customwas decanted
  3. additionby pouring onto a mixture of ice (500 g) and concentrated HCl (30 mL)
  4. customThe solid was collected by suction
  5. washwashed with 1N HCl and water
  6. customrecrystallized in EtOH

Sources & evidence

ORD record
ord-ef1365783e6047d088279ad02ee6802d
Source dataset
uspto-grants-2016_08
Patent number
US09422275B2

Reaction notes

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