Dimethylformamide → Methyl 3-carbamoyl-5-nitrobenzoate

HRID 251827

Reaction equation

HRID 251827 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4ff90498172a4076bdb23340aa885828
Source dataset
uspto-grants-2011_01
Patent number
US07868001B2

Linked notes

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