Triethylamine → N-methoxy-N,3-dimethyl-4-nitrobenzamide

HRID 1507309

Reaktionsgleichung

Reaktionsgleichung von HRID 1507309
C(N(CC)CC)C.[CH3:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12](O)=[O:13].Cl.[CH3:22][NH:23][O:24][CH3:25].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:25][O:24][N:23]([CH3:22])[C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:17]([N+:18]([O-:20])=[O:19])=[C:9]([CH3:8])[CH:10]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 183703-Methyl-4-nitrobenzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Produkt 1

HCID 46318653N-methoxy-N,3-dimethyl-4-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (7.6 mL, 54.65 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (5 g, 27.33 mmol), N,O-dimethylhydroxylamine hydrochloride (2.99 g, 30.06 mmol), and EDCI (6.28 g, 32.79 mmol) in DCM (30 mL). The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHCO3 and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 10 minutes and layers were separated. The aqueous layer was again extracted with DCM. The combined organic layer was dried over Na2SO4, then filtered. The solvent was removed and the residual oil chromatographed (DCM/EtOAc) to provide the title compound as a white solid.

Aufarbeitung

  1. customquenched with saturated aqueous NaHCO3
  2. stirringstirred at room temperature for 30 minutes
  3. additionWater (50 mL) was added
  4. stirringThe mixture was stirred for 10 minutes
  5. customlayers were separated
  6. extractionThe aqueous layer was again extracted with DCM
  7. dry with materialThe combined organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customthe residual oil chromatographed (DCM/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-1fda36faeee44a28a7557e93cef30f90
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221804B2

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