Hydrochloric Acid → (2E)-2-[2-[[5-chloro-3-(trifluoromethyl)-2-pyridinyl]oxymethyl]phenyl]-2-methoxyimino-N-methylacetamide

HRID 1637015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637015
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[N:14][O:15][CH3:16])[C:10]([NH:12][CH3:13])=[O:11].[H-].[Na+].Cl[C:20]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][C:23]([Cl:30])=[CH:22][N:21]=1.Cl>C1COCC1>[Cl:30][C:23]1[CH:24]=[C:25]([C:26]([F:29])([F:27])[F:28])[C:20]([O:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2/[C:9](=[N:14]\[O:15][CH3:16])/[C:10]([NH:12][CH3:13])=[O:11])=[N:21][CH:22]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 110421442,5-dichloro-3-(trifluoromethyl)pyridineHCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

Produkt 1

HCID 22016901(2E)-2-[2-[[5-chloro-3-(trifluoromethyl)-2-pyridinyl]oxymethyl]phenyl]-2-methoxyimino-N-methylacetamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(2-Hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide (300 mg) was dissolved in THF (5 ml). 60% Sodium hydride (65 mg) was added, and the mixture was stirred for 10 minutes. 2,5-Dichloro-3-trifluoromethylpyridine (350 mg) was added, and the mixture was stirred at room temperature for 12 hours, neutralized with 1N-hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to obtain the title compound (398 mg, yield: 74%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4999b3b427434885b3e687af07bc5c74
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06037495

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