Acetyl chloride → HCID 57890444, compound

HRID 1819997Notes

Reaction equation

HRID 1819997 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])=[CH:4][CH:3]=1.[C:19](Cl)(=[O:21])[CH3:20].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:19]([C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:17]=[CH:18][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 795480HCID 795480, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 57890444HCID 57890444, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-N-(2-phenylethyl)benzamide (10.0 g, 32.9 mmol) and acetyl chloride (3.04 ml, 42.7 mmol) in dichloromethane (80 ml) was added aluminum chloride (11.0 g, 82.2 mmol), and the mixture was stirred at room temperature for one day. The reaction mixture was poured into ice, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was powderized with isopropyl ether to give the title compound (9.79 g).

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5bb5756f93ab46deb2cb1e4d7918771f
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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