Acetyl chloride → HCID 13221159, compound

HRID 38437Notes

Reaction equation

HRID 38437 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[C:13]([C:8]1[CH:7]=[CH:6][C:5]([NH:9][C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:2][CH3:1])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11494Acetamide, N-(3-methoxyphenyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 13221159HCID 13221159, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3-Methoxy-phenyl)-acetamide (17.7 g, 107 mmol) in methylene chloride was cooled to zero degrees C., and acetyl chloride (19.0 ml, 268 mmol) was slowly added, followed by aluminum chloride (35.7 g, 268 mmol) in small portions over 15 min. The reaction mixture was stirred 15 minutes at zero degrees, then allowed to warm to room temperature with stirring. The reaction mixture was poured into ice, stirred 35 minutes, and filtered. The solid was washed with water. The filtrate was extracted with EtOAc and solvent was removed under reduced pressure. The combined solids gave N-(4-Acetyl-3-methoxy-phenyl)-acetamide (16.5 g., 74%) as a solid.

Workup

  1. stirringwith stirring
  2. additionThe reaction mixture was poured into ice
  3. stirringstirred 35 minutes
  4. filtrationfiltered
  5. washThe solid was washed with water
  6. extractionThe filtrate was extracted with EtOAc and solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-13baff1e97d44dde8c7fdafb3d01e1a6
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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