AcOH AcOAc → N-(3-Cyano-4-(ethylsulfonyl)phenyl)acetamide
Reaction equation
[CH2:1]([S:3]([C:6]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:7]=1[C:8]#[N:9])(=[O:5])=[O:4])[CH3:2].[C:17](O)(=[O:19])[CH3:18].C(OC(=O)C)(=O)C>[Fe]>[C:8]([C:7]1[CH:10]=[C:11]([NH:14][C:17](=[O:19])[CH3:18])[CH:12]=[CH:13][C:6]=1[S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To 5B (3.60 g, 15.0 mmol) in 1:1 acetic acid/acetic anhydride (150 mL), Fe (4.20 g, 75.2 mmol) was added. The reaction mixture was heated to 100° C. for 2 h then poured into ice. After the ice melted, the product was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4), filtered and concentrated to provide 5C (3.14 g, 83%). LC-MS: 241.18 (M+H)+.