Chloroacetyl chloride → HCID 22163624, compound

HRID 1087766Notes

Reaction equation

HRID 1087766 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:5][C:6]=1[C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)(Cl)Cl>[Cl:23][CH2:24][C:25]([NH:1][C:2]1[S:3][C:4]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:5][C:6]=1[C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:26]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 221636022-Amino-3-(4-methoxybenzoyl)-5-hexylthiophene

Product 1

HCID 22163624HCID 22163624, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 28 g of 2-amino-3-(4-methoxybenzoyl)-5-hexylthiophene in 150 ml of chloroform is added 10 g of chloroacetyl chloride and the mixture is refluxed under heating with stirring for 2 hours. After cooling, the mixture is washed with 5% aqueous sodium hydrogencarbonate solution and sodium chloride solution, and dried over anhydrous magnesium sulfate. After separating by filtration, the filtrate is concentrated under reduced pressure and the residue is crystallized from ethanol to give 16.2 g of 2-chloroacetamido-3-(4-methoxybenzoyl)-5-hexylthiophene as crystals.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating
  3. temperatureAfter cooling
  4. washthe mixture is washed with 5% aqueous sodium hydrogencarbonate solution and sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter separating by filtration
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customthe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-f210c43ef2054ca9859c387df2626f0c
Source dataset
uspto-grants-1990_10
Patent number
US04960770

Reaction notes

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