Dimethylformamide → 2-Methyl-4-nitrobenzamide

HRID 1690263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690263
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C[N:15](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 747904-Nitro-o-toluic acid

Produkt 1

HCID 201651202-Methyl-4-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 2-methyl-4-nitrobenzoic acid suspended in CH2Cl2 under Ar was added DMF then oxalyl chloride. The reaction was stirred at room temperature 1.5 hours then the solvent was evaporated. The residue was dissolved in THF and ammonia gas was bubbled through the reaction for 15 minutes. The solvent was evaporated and the residue partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The extracts were dried (MgSO4), filtered and evaporated. Column chromatography (SiO2, 0-100% EtOAc/Hex) gave pure 2-methyl-4-nitrobenzamide (E111).

Aufarbeitung

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in THF
  3. customammonia gas was bubbled through the reaction for 15 minutes
  4. customThe solvent was evaporated
  5. customthe residue partitioned between EtOAc and water
  6. extractionThe aqueous layer was extracted with EtOAc
  7. dry with materialThe extracts were dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6401720d8f0c43caa91650ddddc2842f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153656B2

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