Dimethylformamide → Methyl 3-carbamoyl-5-nitrobenzoate

HRID 251827

Reaktionsgleichung

Reaktionsgleichung von HRID 251827
[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

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4ff90498172a4076bdb23340aa885828
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868001B2

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