Methylamine → 2-bromo-N-methyl-3-nitrobenzamide

HRID 2036571

Reaktionsgleichung

Reaktionsgleichung von HRID 2036571
[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CN.O1CCCC1.C[CH2:22][N:23](C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:23][CH3:22])=[O:5]

Komponenten

7

Edukt 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 684522-Bromo-3-nitrobenzoic acidHCID 81531Diisopropylethylamine

Produkt 1

HCID 674334472-bromo-N-methyl-3-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-3-nitrobenzoic acid (0.974 g, 3.96 mmol) in DMF (3 mL) was added methylamine, 2.0 m solution in tetrahydrofuran (2.97 mL, 5.94 mmol), 1,1′-dimethyltriethylamine (1.38 mL, 7.92 mmol) and (1H-benzo[d]-[1,2,3]triazol-1-yloxy)tripyrrolidin-1-ylphosphonium hexafluorophosphate(V) (2.47 g, 4.75 mmol) and the resulting mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel column using DCM/EtOAc-DCM (1:1) as eluent to give 2-bromo-N-methyl-3-nitrobenzamide: LC-MS (ESI) m/z 261.0 [M+H]+.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-cc6e0d8e9c424a57af304fc3f446ea1c
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575183B2

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