Isopropyl iodide → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(prop-2-ylamino)-4-trifluoroacetylpyrazole

HRID 377668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377668
[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+].I[CH:34]([CH3:36])[CH3:35]>O>[C:19]([C:4]1[C:3]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:2]([NH:1][CH:34]([CH3:36])[CH3:35])[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

5

Edukt 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 186994595-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

Produkt 1

HCID 193564843-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(prop-2-ylamino)-4-trifluoroacetylpyrazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole (1 g) in anhydrous N,N-dimethylformnamide (4 ml) at room temperature was added potassium carbonate (0.7 g), then 2-iodopropane (190 μl). The mixture was stirred at room temperature for 48 hours. 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 solid, m.p 136-137° 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-4f5d029b5b4546a89ed5a738c61e8bbe
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028096

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