Dimethylamine → N,N,3-trimethyl-4-nitrobenzamide

HRID 510475

Reaktionsgleichung

Reaktionsgleichung von HRID 510475
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].C[CH2:15][N:16](C(C)C)[CH:17](C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CNC>CN(C=O)C.O>[CH3:15][N:16]([CH3:17])[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([CH3:1])[CH:3]=1

Komponenten

7

Edukt 4

HCID 674DimethylamineHCID 183703-Methyl-4-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 786992N,N,3-trimethyl-4-nitrobenzamideAusbeute 73,17 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-methyl-4-nitrobenzoic acid (0.5 g, 2.76 mmol) in DMF (5 mL) was added DIPEA (1.06 g, 8.28 mmol), followed by HATU (1.57 g, 4.14 mmol) and dimethylamine (0.24 g, 5.52 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was then diluted with water and extracted with EtOAc. The organic layer was washed with brine, then concentrated to provide crude material which was further purified by column chromatography (silica:100-200 mesh, MeOH:DCM 8-10%), to afford the title compound (0.42 g, 73.17%). LCMS (ES+) 209 (M+H)+, RT 1.92 minutes (method 3).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated
  4. customto provide crude material which
  5. customwas further purified by column chromatography (silica:100-200 mesh, MeOH:DCM 8-10%)

Quellen und Nachweise

ORD-Eintrag
ord-15264fb989334572a52b0318e5672d67
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096614B2

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