Dimethylformamide → Methyl 3-carbamoyl-5-nitrobenzoate

반응식

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:8](O)=[O:9])=[O:4].O=S(Cl)Cl.C[N:22](C=O)C>>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:7]([C:8](=[O:9])[NH2:22])[CH:6]=1

참가 물질

반응물 3

HCID 6228Dimethylformamide

HCID 24386Thionyl Chloride

HCID 747761,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl ester

생성물 1

HCID 3741295Methyl 3-carbamoyl-5-nitrobenzoate수율 85%

실험 절차

A mixture of 3-methoxycarbonyl-5-nitrobenzoic acid (44 mmol), SOCl2 (40 mL) and DMF (1 mL) was heated to reflux for 2 hours. Then the excessive SOCl2 was removed under reduced pressure. The residue was dissolved in DCM (80 mL), and added with NH3.H2O (15 mL) dropwise after cooling by ice-water. After addition, it was continued to stir 5 min. The resulting mixture was filtrated to give methyl-3-carbamoyl-5-nitrobenzoate in 85% yield.