Dimethylformamide → Methyl 3-carbamoyl-5-nitrobenzoate

HRID 251827

反応式

HRID 251827 の反応式
[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

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 747761,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl ester

生成物 1

HCID 3741295Methyl 3-carbamoyl-5-nitrobenzoate収率 85%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ff90498172a4076bdb23340aa885828
出典データセット
uspto-grants-2011_01
特許番号
US07868001B2

関連ノート

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