Chloroacetyl chloride → N-[[5-(2-Chloroacetyl)thien-2-yl]methyl]acetamide

HRID 2413893Notes

Reaction equation

HRID 2413893 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Cl:11][CH2:12][C:13](Cl)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:1]([NH:4][CH2:5][C:6]1[S:7][C:8]([C:13](=[O:14])[CH2:12][Cl:11])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 30617N-[(Thiophen-2-yl)methyl]ethanimidic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 4962027N-[[5-(2-Chloroacetyl)thien-2-yl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g of 2-acetylaminomethylthiophene and 4.4 g of chloroacetylchloride in 100 ml of dichloromethane is added a small portion of 8.6 g of anhydrous aluminum chloride at room temperature, and the mixture is refluxed with stirring for an hour and poured into ice-cold water. The precipitated crystals are collected by filtration to give 2-acetylaminomethyl-5-chloroacetylthiophene, melting at 146°-148° C.

Workup

  1. temperaturethe mixture is refluxed
  2. additionpoured into ice-cold water
  3. filtrationThe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-d963bcb06563414fb8f5697f7d7b6685
Source dataset
uspto-grants-1988_01
Patent number
US04720493

Reaction notes

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