Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 178432147, compound

HRID 37216

Reaction equation

HRID 37216 reaction equation
[N:1]1([CH:6]([C:10]2[CH:11]=[C:12]([NH2:17])[C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.[ClH:18].[C:19](=N)(OCC)[CH3:20]>C(O)C>[ClH:18].[ClH:18].[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]3[NH:16][C:19]([CH3:20])=[N:17][C:12]=3[CH:11]=2)[CH:7]([CH3:8])[CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 145184264-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamine

Product 1

HCID 178432147HCID 178432147, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  1. temperatureat reflux temperature
  2. customAfter evaporation
  3. customto dry
  4. extractionThe product was extracted three times with 120 parts of trichloromethane
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. additionThe residue was convened into the hydrochloride salt in a mixture of 2-propanone and ethanol
  13. filtrationThe salt was filtered off
  14. customcrystallized from a mixture of ethanol and 2-propanone
  15. filtrationThe product was filtered off
  16. customdried

Sources & evidence

ORD record
ord-0ce4a9a0b859482abf544ddf922c98a5
Source dataset
uspto-grants-1995_05
Patent number
US05420147

Linked notes

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