Reaktion #1285359

Reaktionsgleichung

4-[2-hydroxyadamant-2-yl-1-(1,2,4-triazolyl)methyl]benzonitrile

thionyl chloride

→

4-[2-adamantylidene-1-(1,2,4-triazolyl)methyl]benzonitrile

Ausbeute 62.2%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThen the mixture is concentrated to dryness in an oil pump vacuum
2. 2
   workup.DISSOLUTIONdissolved in 50 ml of dichloromethane
3. 3
   workup.ADDITIONdiluted with water
4. 4
   Extraktionextracted three times with ethyl acetate
5. 5
   Waschenwashed with sodium chloride solution
6. 6
   Trocknendried over sodium sulfate
7. 7
   Einengenconcentrated to dryness under vacuum
8. 8
   Sonstigechromatographed on silica gel with hexane/ethyl acetate

Vorschrift

9 g of crude 4-[2-hydroxyadamant-2-yl-1-(1,2,4-triazolyl)methyl]benzonitrile is dissolved at 0° in 50 ml of dichloromethane and stirred at 0° with 24 ml of thionyl chloride for 1 hour. Then the mixture is concentrated to dryness in an oil pump vacuum, dissolved in 50 ml of dichloromethane, stirred for 2 hours with 32 ml of triethylamine, diluted with water, extracted three times with ethyl acetate, washed with sodium chloride solution, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, yielding 5.3 g of 4-[2-adamantylidene-1-(1,2,4-triazolyl)methyl]benzonitrile as the free base, mp 130°, which is converted with hydrochloric acid into the hydrochloride, mp 105°.

Quelle