Dimethylformamide → Methyl 3-carbamoyl-5-nitrobenzoate

HRID 251827

반응식

HRID 251827 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

4

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 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.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThen the excessive SOCl2 was removed under reduced pressure
  4. dissolutionThe residue was dissolved in DCM (80 mL)
  5. additionadded with NH3.H2O (15 mL) dropwise
  6. temperatureafter cooling by ice-water
  7. additionAfter addition, it
  8. filtrationThe resulting mixture was filtrated

출처 및 근거

ORD 기록
ord-4ff90498172a4076bdb23340aa885828
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868001B2

연결된 노트

불러오는 중…