Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 178432090, compound

HRID 1723142Notes

Reaction equation

HRID 1723142 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([N:17]2[CH:21]=[CH:20][N: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][CH:7]=1.Cl.[C:23](=N)(OCC)[CH3:24]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[C:9]2[CH:14]=[CH:13][C:12]3[NH:15][C:23]([CH3:24])=[N:16][C:11]=3[CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 14500563HCID 14500563, compound

Product 1

HCID 178432090HCID 178432090, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.99 parts of 4-[(3-chlorophenyl)(1H-imidazol-1-yl)methyl]-1,2-benzenediamine, 1.85 parts of ethyl ethanimidate hydrochloride and 40 parts of methanol was stirred for 16 hours at room temperature. The solvent was evaporated and the residue was dissolved in a dilute hydrochloric acid solution. The whole was alkalized with ammonia and 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 trichloromethane, methanol and methanol saturated with ammonia (90:5:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was dried in vacuo, yielding 2.9 parts (89.8%) of 5-[(3-chlorophenyl)(1H-imidazol-1-yl)methyl]-2-methyl-1H-benzimidazole; mp. 117.1° C. (compound 122).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in a dilute hydrochloric acid solution
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane, methanol and methanol saturated with ammonia (90:5:5 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-813b3d2d9fa548a6ad6710bafa6a4e2b
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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