Water → 5-Amino-4-cyano-1-(5-trimethylsilyl-4-pentynyl)pyrazole

HRID 464104

Reaktionsgleichung

Reaktionsgleichung von HRID 464104
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]#[N:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:16][CH2:17][CH2:18][C:19]#[C:20][Si:21]([CH3:24])([CH3:23])[CH3:22].O>CN(C=O)C.C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:6]([CH2:16][CH2:17][CH2:18][C:19]#[C:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:5]=[CH:4][C:3]=1[C:7]#[N:8]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 855155-Amino-4-cyanopyrazoleHCID 11140046Silane, (5-iodo-1-pentynyl)trimethyl-

Produkt 1

HCID 202638335-Amino-4-cyano-1-(5-trimethylsilyl-4-pentynyl)pyrazoleAusbeute 20,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 5-amino-4-cyanopyrazole (10 g) and finely ground anhydrous potassium carbonate (38 g) in dry DMF (100 ml) was treated with 5-iodo-1-trimethylsilyl-1-pentyne (25 g) and the mixture was stirred under nitrogen for two days at room temperature. The reaction mixture was then poured into water and the product extracted into ethyl acetate. The extract was washed with water and then with brine, dried over Na2SO4, and evaporated to give a semisolid brown residue. This solid was taken up in chloroform and filtered through a short plug of silica gel. Evaporation of the chloroform left a tan solid comprising a mixture of the isomeric compounds 5-amino-4-cyano-1-(5-trimethylsilyl-4-pentynyl)pyrazole and 3-amino-4-cyano-1-(5-trimethylsilyl-4-pentynyl)pyrazole. Fractional recrystallization from ethyl acetate/hexane gave 4.66 grams of the desired 5-amino-4-cyano-1-(5-trimethylsilyl-4-pentynyl)pyrazole: mp 125°-127°.

Aufarbeitung

  1. extractionthe product extracted into ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialwith brine, dried over Na2SO4
  4. customevaporated
  5. customto give a semisolid brown residue
  6. filtrationfiltered through a short plug of silica gel
  7. customEvaporation of the chloroform
  8. waitleft a tan solid comprising
  9. additiona mixture of the isomeric compounds 5-amino-4-cyano-1-(5-trimethylsilyl-4-pentynyl)pyrazole and 3-amino-4-cyano-1-(5-trimethylsilyl-4-pentynyl)pyrazole
  10. customFractional recrystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-0bebbb73c7e44a5eadcc029bcc5de8fb
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04546104

Verknüpfte Notizen

Wird geladen…