Acetyl chloride → N-(4-Acetyl-3-methylphenyl)acetamide

HRID 1492419Notes

Reaction equation

HRID 1492419 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]([CH3:11])=[O:10])[CH:3]=1.[C:12](Cl)(=[O:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[C:12]([C:7]1[CH:6]=[CH:5][C:4]([NH:8][C:9](=[O:10])[CH3:11])=[CH:3][C:2]=1[CH3:1])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10843N-(3-Methylphenyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2737381N-(4-Acetyl-3-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

The reaction was run in a 500 mL 3 neck round bottom (RB) fitted with a mechanical stirrer and reflux condenser. To 45 g (301.6 mmol) of 3-methylacetanilide in 240 mL of carbon disulfide under argon at RT was added 38.6 mL (542.8 mmol) of acetyl chloride with stirring. To the solution was then added 145 g (1.09 mol) of aluminum chloride in small portions over a 1 h period. After addition was complete the mixture was refluxed for 1 h and then allowed to cool and stand for 1 h. The supernatant carbon disulfide layer was decanted off and the very dark viscous lower layer was poured into a mixture of cracked ice and hydrochloric acid. The precipitate was collected and washed with 1 L of water. The solid was dried under high vacuum for 30 h at RT no provide 52.17 g (90%) of title amide in the form of a light tan solid which is used as the crude material in the following reaction.

Workup

  1. customfitted with a mechanical stirrer
  2. temperaturereflux condenser
  3. additionAfter addition
  4. temperaturewas refluxed for 1 h
  5. temperatureto cool
  6. customThe supernatant carbon disulfide layer was decanted off
  7. additionthe very dark viscous lower layer was poured into a mixture of cracked ice and hydrochloric acid
  8. customThe precipitate was collected
  9. washwashed with 1 L of water
  10. dry with materialThe solid was dried under high vacuum for 30 h at RT no provide 52.17 g (90%) of title amide in the form of a light tan solid which
  11. customis used as the crude material in the following reaction

Sources & evidence

ORD record
ord-76db2aa2dc2342a2b660e42583bc2dc5
Source dataset
uspto-grants-1994_12
Patent number
US05374628

Reaction notes

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