Chloroacetyl chloride → HCID 19439696, compound

HRID 1734019Notes

Reaction equation

HRID 1734019 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:10][C:11]1[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=1[CH2:13][NH:14][C:15](=[O:17])[CH3:16]>ClC(Cl)C>[Cl:1][CH2:2][C:3]([C:20]1[CH:19]=[CH:18][C:12]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])=[C:11]([CH3:10])[CH:21]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15640187HCID 15640187, compound

Product 1

HCID 19439696HCID 19439696, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Chloroacetyl chloride (17 g) was added dropwise to a mixture of aluminum chloride (13.3 g) in dichloroethane (60 ml) at ambient temperature under stirring and the mixture was stirred for one hour. To the resulting mixture was added N-(2-methylbenzyl)acetamide (13.3 g) at ambient temperature and the mixture was stirred at 25° to 50° C. for 1.5 hours. The reaction mixture was poured into ice water and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue was washed with ethyl acetate and diisopropyl ether to give N-(4-chloroacetyl-2-methylbenzyl)acetamide (5.8 g).

Workup

  1. stirringthe mixture was stirred for one hour
  2. stirringthe mixture was stirred at 25° to 50° C. for 1.5 hours
  3. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solvent was concentrated in vacuo
  7. washthe residue was washed with ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-1af282e4fef74a4b81641824670c1b62
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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