Acetyl chloride → 4'-Acetamido-2'-methylacetophenone

反応式

[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]

参加物

実験手順

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.