反应详情

To 184 parts of cold (10° C., ice bath) concentrated sulfuric acid were added portionwise 75 parts of 1-[(3-methoxyphenyl)methyl]-1H-imidazole mononitrate during 1 hour. Upon complete addition, stirring was continued for 30 minutes at 10° C. 15 Parts ofconcentrated nitric acid were added dropwise during 30 minutes at 15° C. Uponcompletion, the whole was stirred for 30 minutes at 10° C. The reaction mixture was poured into 1500 parts of crushed ice and the whole was treatedwith an ammonium hydroxide solution. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of ethyl acetate, methanol and methanol, saturated with ammonia, (95:2.5:2.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated in vacuo. The residue was stirred in 45 parts of ethyl acetate. The precipitated product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 28.2 parts (40.3%) of 1-[(3-methoxy-4-nitrophenyl)methyl]-1H-imidazole (int. 145).

1. additionUpon complete addition
2. stirringUponcompletion, the whole was stirred for 30 minutes at 10° C
3. additionThe reaction mixture was poured into 1500 parts of crushed ice
4. extractionThe product was extracted with dichloromethane
5. customThe extract was dried
6. filtrationfiltered
7. customevaporated
8. customThe residue was purified by column chromatography over silica gel using
9. additiona mixture of ethyl acetate, methanol and methanol
10. customThe pure fractions were collected
11. customthe eluent was evaporated in vacuo
12. stirringThe residue was stirred in 45 parts of ethyl acetate
13. filtrationThe precipitated product was filtered off
14. washwashed with 2,2'-oxybispropane
15. customdried