3'-Aminoacetophenone → N-(3-acetylphenyl)furan-2-carboxamide
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1)=[O:3].C(N(C(C)C)C(C)C)C.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](Cl)=[O:26]>C(Cl)Cl>[C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:25]([C:21]2[O:20][CH:24]=[CH:23][CH:22]=2)=[O:26])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 1 g of 3-aminoacetophenone in 20 mL of CH2Cl2 was added 5 mL of ethyl-di-iso-propylamine. To the stirred reaction mixture was then added 1 mL of 2-furoyl chloride which was allowed to stir at 25° C. for 8 h. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (CH2Cl2) to yield 900 mg of furan-2-carboxylic acid (3-acetyl-phenyl)-amide as a white solid. 1H NMR (CDCl3, 500 MHz) δ 8.11 (1 H, br s), 8.09 (1H, t, J=2 Hz), 7.93 (1 H, m), 7.66 (1H, m), 7.47 (1 H, m), 7.20 (1 H, m), 6.52 (1 H, m), 2.56 (3H, s) ppm.
Workup
- customTo the stirred reaction mixture
- concentrationThe reaction mixture was concentrated in vacuo
- customthe residue was purified by silica gel chromatography (CH2Cl2)
Sources & evidence
- ORD record
- ord-a1fe85e8df5c4a2a9721ee61981a415a
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312227B2
Reaction notes
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