Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 178432215, compound

HRID 1723100Notes

Reaction equation

HRID 1723100 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9](C2C=CC=C(F)C=2)=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].Cl.[C:19](=N)(OCC)[CH3:20]>CO>[CH3:19][C:20]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([CH:9]=[O:10])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 10775793HCID 10775793, compound

Product 1

HCID 178432215HCID 178432215, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(a-1) A mixture of 20 parts of (3,4-diaminophenyl) (3-fluorophenyl) methanone, 27 parts of ethyl ethanimidate hydrochloride and 80 parts of methanol was stirred for 17 hours at reflux temperature. The reaction mixture was filtered and the filtrate was evaporated. The residue was taken up in a potassium carbonate solution 10% and the product was extracted with ethyl acetate. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 15.6 parts (70.5%) of 3-fluorophenyl) (2-methyl-1H-benzimidazol-5-yl)methanone as a residue (int. 34).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. extractionthe product was extracted with ethyl acetate
  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 dichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-67a9f6f5ec3f4eacafc605d0104840a7
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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