Water → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylamino-4-trifluoroacetylpyrazole

HRID 377665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377665
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21](=[O:26])[C:22]([F:25])([F:24])[F:23].[C:27](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[C:19]([C:4]1[C:3]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:2]([NH:1][CH3:27])[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=1)#[N:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 186994595-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

Produkt 1

HCID 193564703-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylamino-4-trifluoroacetylpyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole (1 g) in anhydrous N,N-dimethylformamide (5 ml) at room temperature was added potassium carbonate (0.69 g), then iodomethane (97 μl). The mixture was stirred at room temperature for one hour. Water (30 ml) was then added, and the mixture was extracted with ether (50 ml, ×2). The combined organic layers were washed with water (30 ml, ×2), and evaporated. The residue was purified by column chromatography on silica gel (50 g) eluted with dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a white solid, m.p 160-161° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ether (50 ml, ×2)
  2. washThe combined organic layers were washed with water (30 ml, ×2)
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel (50 g)
  5. washeluted with dichloromethane
  6. customCombination and evaporation of suitable fractions

Quellen und Nachweise

ORD-Eintrag
ord-621092639a1e41c6addde6a015662308
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028096

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