Reaktion #324179

Reaktionsgleichung

water

4-(4-fluorophenyl)-5-(2-thienyl)-1H-2-imidazolethiol

diisopropylamine

tetrafluoroethylene

→

4-(4-Fluorophenyl)-2-(1,1,2,2-tetrafluoroethylthio)-5-(2-thienyl)-1H-imidazole

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe pressure dropped from 160 psi to 0 in 1.5 hrs
2. 2
   Filtrationfiltered
3. 3
   Waschenwashed with water
4. 4
   workup.DISSOLUTIONThe solid was dissolved in chloroform
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated
7. 7
   workup.ADDITIONdiluted with 1-chlorobutane
8. 8
   SonstigeThe crystalline product was collected
9. 9
   SonstigeThe residue from the filtrate was chromatographed on silica gel (Silicar CC-4)
10. 10
    Sonstigeto give 4.1 g, m.p. 167.5°-170° C
11. 11
    SonstigeThe combined 6.5 g was crystallized from 1-chlorobutane
12. 12
    Sonstigeto give 5.6 g, m.p. 167°-168.5° C.

Vorschrift

A solution of 14.0 g of 4-(4-fluorophenyl)-5-(2-thienyl)-1H-2-imidazolethiol in 40 ml of dimethylformamide and 1.5 g of diisopropylamine was pressured in a bomb with 4 g of tetrafluoroethylene. The pressure dropped from 160 psi to 0 in 1.5 hrs. The solution was poured into water, stirred until most of gum solidified, filtered and washed with water. The solid was dissolved in chloroform, dried over anhydrous sodium sulfate, concentrated and diluted with 1-chlorobutane. The crystalline product was collected; yield 2.5 g, m.p. 164°-168° C. The residue from the filtrate was chromatographed on silica gel (Silicar CC-4) using chloroform to give 4.1 g, m.p. 167.5°-170° C. The combined 6.5 g was crystallized from 1-chlorobutane to give 5.6 g, m.p. 167°-168.5° C.

Quelle