Acetyl chloride → N-[2-(5-Chloro-2-phenylbenzo[b]thiophen-3-yl)ethyl]acetamide

HRID 985759Notes

Reaction equation

HRID 985759 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:8]([CH2:17][CH2:18][NH2:19])[C:7]=2[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[C:27](Cl)(=[O:29])[CH3:28]>O.ClCCl>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:8]([CH2:17][CH2:18][NH:19][C:27](=[O:29])[CH3:28])[C:7]=2[CH:20]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 124121842-(5-Chloro-2-phenyl-1-benzothiophen-3-yl)-1-ethanamine Hydrochloride

Product 1

HCID 21917005N-[2-(5-Chloro-2-phenylbenzo[b]thiophen-3-yl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

The compound obtained in Step E is dissolved in a mixture of water/dichloromethane (2/3); 2 eq. of potassium carbonate are then added and 2 eq. acetyl chloride are added dropwise. After stirring for 2 hours at ambient temperature, the 2 phases are separated; the organic phase is washed with 1M HCl and then with water, until the washing waters are neutral, and is then dried as over MgSO4 and evaporated. The residue obtained is purified by chromatography on silica gel.

Workup

  1. customthe 2 phases are separated
  2. washthe organic phase is washed with 1M HCl
  3. dry with materialis then dried as over MgSO4
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-dcd157902f7949469a26b4615bc85ac0
Source dataset
uspto-grants-2005_03
Patent number
US06872851B1

Reaction notes

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