반응 #349152

반응 방정식

N,N,N',N'-tetramethylethylenediamine

oxalate

4,4'-dichlorobenzophenone

butyl lithium

1-(p-chlorobenzyl)imidazole

→

1-(p-Chlorobenzyl)-α,α-bis-(p-chlorophenyl)imidazole-2-methanol

용매

tetrahydrofuran

tetrahydrofuran

n-hexane

반응 조건

후처리

1. 1
   기타In the course of one hour, 64 ml
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas continued for one hour
4. 4
   기타the cooling means was removed
5. 5
   workup.WAITthe reaction mixture was kept standing overnight at room temperature
6. 6
   workup.ADDITIONof water were added
7. 7
   기타the organic phase was separated off
8. 8
   농축concentrated
9. 9
   workup.ADDITIONThe residue was suspended in a mixture of water and diethyl ether
10. 10
    기타The solid matter formed
11. 11
    여과was filtered off
12. 12
    기타the ethereal layer was separated off
13. 13
    건조dried over sodium sulphate
14. 14
    농축concentrated
15. 15
    기타The residue was twice crystallised from methanol

실험 절차

In the course of one hour, 64 ml. (0.105 mol) of 15% butyl lithium in n-hexane were added dropwise at -65° to -70° C. and under a nitrogen atmosphere, to a solution of 19.3 g (0.1 mol) of 1-(p-chlorobenzyl)imidazole (prepared from the oxalate described under (A) and 12.2 g (0.105 mol) of N,N,N',N'-tetramethylethylenediamine in 150 ml. of anhydrous tetrahydrofuran. The reaction mixture was stirred for one hour and then a suspension of 25.1 g (0.1 mol) of 4,4'-dichlorobenzophenone in 150 ml. of anhydrous tetrahydrofuran was added quickly under the same reaction conditions. Stirring was continued for one hour and then the cooling means was removed and the reaction mixture was kept standing overnight at room temperature. 20 ml. of water were added and the organic phase was separated off and concentrated. The residue was suspended in a mixture of water and diethyl ether. The solid matter formed was filtered off and the ethereal layer was separated off, dried over sodium sulphate and concentrated. The residue was twice crystallised from methanol. 1-(p-Chlorobenzyl)-α,α-bis-(p-chlorophenyl)imidazole-2-methanol was obtained. Melting point 171°-173° C.

출처