Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 178503472, compound

HRID 1723131Notes

Reaction equation

HRID 1723131 reaction equation
[CH3:1][S:2][C:3]1[N:4]([CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=2)[CH:5]=[CH:6][N:7]=1.Cl.[C:24](=N)(OCC)[CH3:25]>CO>[CH3:24][C:25]1[NH:15][C:12]2[CH:13]=[CH:14][C:9]([CH:8]([N:4]3[CH:5]=[CH:6][N:7]=[C:3]3[S:2][CH3:1])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][C:11]=2[N:16]=1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 20026602HCID 20026602, compound

Product 1

HCID 178503472HCID 178503472, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(a-6) A mixture of 5.6 parts of (+)-4-[[2-(methylthio)-1H-imidazol-1-yl]-phenylmethyl]-1,2-benzendiamine, 2.8 parts of ethyl ethanimidate hydrochloride and 60 parts of methanol was stirred first overnight at room temperature and then for 2 hours at reflux temperature. After cooling, the reaction mixture was evaporated. The residue was treated with alkaline water and the product was extracted three times with dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 3.2 parts (79.3%) of (+)-2-methyl-5-[[2-(methylthio)-1H-imidazol-1-yl]phenylmethyl]-1H-benzimidazole as a residue (int. 144).

Workup

  1. temperaturefor 2 hours at reflux temperature
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated
  4. additionThe residue was treated with alkaline water
  5. extractionthe product was extracted three times with dichloromethane
  6. customThe combined extracts were dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of dichloromethane and methanol (96:4 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated

Sources & evidence

ORD record
ord-0bb3cf263ffc4c2d896ad89b466b61f0
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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