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

HRID 1242683Notes

Reaction equation

HRID 1242683 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 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 over MgSO4
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f525141400f44f2d9490b868c2361e7c
Source dataset
uspto-grants-2006_10
Patent number
US07115752B2

Reaction notes

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