Pyridine → N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide

HRID 585973

Reaktionsgleichung

Reaktionsgleichung von HRID 585973
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].N1C=CC=CC=1>C(Cl)Cl.C(OCC)C>[CH3:18][O:17][N:16]([CH3:15])[C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Produkt 1

HCID 14069348N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(Trifluoromethyl)benzoyl chloride (5.0 g, 23.9 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.55 g, 26.3 mmol, 1.1 eq.) were combined in CH2Cl2 (200 mL) at 0° C. and treated with pyridine (4.3 mL, 52.6 mmol). After stirring for 2 hours, the mixture was allowed to attain ambient temperature, diluted with diethyl ether and washed with water, aqueous HCl, and water. the organic phase was separated and concentrated to provide the title compound which was used directly in the next step. 1H NMR (300 MHz, d6-DMSO) 7.90 (m, 4H), 3.52 (s, 3H), 3.28 (s, 3H); MS (DCI/NH3) m/e 234 (M+H)+.

Aufarbeitung

  1. customto attain ambient temperature
  2. washwashed with water, aqueous HCl, and water
  3. customthe organic phase was separated
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ff9ef132d9564af882d03ceee67b3dc2
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933311B2

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