Chloroacetyl chloride → N-[5-Chloro-4-(2-chloro-acetyl)-2-methyl-phenyl]-acetamide

HRID 2211906

Reaction equation

HRID 2211906 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Cl:1][C:2]1[C:3]([C:15](=[O:16])[CH2:14][Cl:13])=[CH:4][C:5]([CH3:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 80000N-(5-Chloro-2-methylphenyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21963317N-[5-Chloro-4-(2-chloro-acetyl)-2-methyl-phenyl]-acetamideYield 76%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To N-(5-Chloro-2-methyl-phenyl)-acetamide (30 g, 163.37 mmol) in carbondisulfide (1200 mL) was added chloroacetylchloride (19.50 mL, 245.05 mmol) followed by anhydrous aluminum chloride powder (65.35 g, 490.11 mmol) in one portion at rt. The reaction was heated to reflux for 3 h after which the reaction was cooled and the solvent decanted. The remaining residue was carefully hydrolyzed with cold H2O (500 mL) with vigorous stirring to give a white/gray solid suspension which was collected by filtration and dried in vacuo to give desire product (32.15 g, 123.6 mmol). Yield=76%; 1H NMR (400 MHz, CDCl3) δ 8.28 (bs, 1H, NH), 7.47 (s, 1H), 7.24 (s, 1H), 4.73 (s, 2H), 2.25 (s, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 h after which the reaction
  3. temperaturewas cooled
  4. customthe solvent decanted
  5. customto give a white/gray solid suspension which
  6. filtrationwas collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3e49c8f06068403990aa7647d1663f22
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Linked notes

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