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

HRID 377666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377666
[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(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[CH:34]=[CH2:35].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][CH2:35][CH:34]=[CH2:33])[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 7841Allyl bromideHCID 11430Potassium CarbonateHCID 186994595-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

Produkt 1

HCID 193564653-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(prop-2-enylamino)-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 (4 ml) at room temperature was added potassium carbonate (0.7 g), then allyl bromide (165 μl). The mixture was stirred at room temperature for 40 minutes. Water (50 ml) was then added, and the mixture was extracted with ether (50 ml, ×2). The combined organic layers were washed with water (50 ml), dried (Na2SO4), filtered 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 very pale yellow/white solid, m.p 115-116° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ether (50 ml, ×2)
  2. washThe combined organic layers were washed with water (50 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (50 g)
  7. washeluted with dichloromethane
  8. customCombination and evaporation of suitable fractions

Quellen und Nachweise

ORD-Eintrag
ord-73a0c92fcdea4e8991d202c0cc694275
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028096

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