Acetyl chloride → HCID 18423154, compound

HRID 1282055Notes

Reaction equation

HRID 1282055 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[C:9]1([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClC(Cl)C>[C:5]([C:12]1[CH:13]=[CH:14][C:9]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:10][CH:11]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11500N-BenzylacetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18423154HCID 18423154, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a suspension of aluminum chloride (22.3 g) in dichloroethane (40 ml) was added acetylchloride (7.1 ml). Thereto was added a solution of N-phenylmethylacetamide (10 g) in dichloroethane (20 ml) at 10-15° C. over 20 min. This reaction mixture was stirred at room temperature for 6 hr and poured into ice water (100 ml). The mixture was extracted with chloroform (100 ml×3). The chloroform layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a black brown oil (15.5 g). The obtained residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol=20:1) to give the title compound (6.48 g) as a black brown solid.

Workup

  1. extractionThe mixture was extracted with chloroform (100 ml×3)
  2. washThe chloroform layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c9d7871c55da4fd48a1f576731e8dc01
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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