반응 #65494

반응 방정식

4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamine

ethyl ethanimidate hydrochloride

→

5-[1-(1H-imidazol-1yl)-2-methylpropyl]-2-methyl-1H-benzimidazole dihydrochloride

수율 44.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도at reflux temperature
2. 2
   기타After evaporation
3. 3
   기타to dry
4. 4
   추출The product was extracted three times with 120 parts of trichloromethane
5. 5
   기타The combined extracts were dried
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The residue was purified by column chromatography over silica gel using
9. 9
   workup.ADDITIONa mixture of trichloromethane and methanol (95:5 by volume) as eluent
10. 10
    기타The pure fractions were collected
11. 11
    기타the eluent was evaporated
12. 12
    workup.ADDITIONThe residue was convened into the hydrochloride salt in a mixture of 2-propanone and ethanol
13. 13
    여과The salt was filtered off
14. 14
    기타crystallized from a mixture of ethanol and 2-propanone
15. 15
    여과The product was filtered off
16. 16
    기타dried

실험 절차

A mixture of 6.2 parts of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamine, 6.5 parts of ethyl ethanimidate hydrochloride and 80 parts of ethanol was stirred for 3 hours at reflux temperature. After evaporation to dry, the residue was taken up in water and sodium carbonate. The product was extracted three times with 120 parts of trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was convened into the hydrochloride salt in a mixture of 2-propanone and ethanol. The salt was filtered off and crystallized from a mixture of ethanol and 2-propanone. The product was filtered off and dried, yielding 4 parts (44% ) of 5-[1-(1H-imidazol-1yl)-2-methylpropyl]-2-methyl-1H-benzimidazole dihydrochloride.monohydrate; mp. 214.8° C. (comp. 22).

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