Acetyl chloride → HCID 13221159, compound

HRID 81852Notes

Reaction equation

HRID 81852 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-f1a539272cc84c67a0729afb79c67f70
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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