Triethylamine → N-Methoxy-N-methyl-2-(trifluoromethyl)isonicotinamide

HRID 1478509

Reaktionsgleichung

Reaktionsgleichung von HRID 1478509
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][N:11]=1)[C:6](O)=[O:7].Cl.[CH3:15][NH:16][O:17][CH3:18].Cl.C(C(NCCCN(C)C)=N)C.CCN(CC)CC.[NH4+].[Cl-]>C(Cl)Cl>[CH3:18][O:17][N:16]([CH3:15])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][N:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 147614472-(Trifluoromethyl)pyridine-4-carboxylic acidHCID 178458058HCID 178458058, Verbindung

Produkt 1

HCID 86716069N-Methoxy-N-methyl-2-(trifluoromethyl)isonicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-(trifluoromethyl)isonicotinic acid (1.03 g, 5.39 mmol), N,O-dimethylhydroxylamine hydrochloride (0.800 g, 8.20 mmol) and N′(ethylcarbonimidoyl)-N,N-dimethyl-1,3-propanediamine hydrochloride (EDCI, 1.35 g, 7.04 mmol) in CH2Cl2 (30 mL) was added Et3N (1.90 mL, 13.7 mmol), and the mixture immediately turned clear. After stirring at room temperature overnight, NH4Cl (aqueous) was added. The mixture was stirred vigorously for a while, and white solid was then filtered off. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic phases were washed with brine, and the aqueous layer was back extracted with CH2Cl2. The organic phases were combined, dried (Na2SO4), filtered, concentrated, and purified by flash column chromatography (40 g silica gel column, 40-70% EtOAc in heptanes) to afford the title compound as a clear oil.

Aufarbeitung

  1. stirringThe mixture was stirred vigorously for a while, and white solid
  2. filtrationwas then filtered off
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined organic phases were washed with brine
  6. extractionthe aqueous layer was back extracted with CH2Cl2
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash column chromatography (40 g silica gel column, 40-70% EtOAc in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-b45158f30e394d7c86e93e30c72b6f83
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403816B2

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