Ethanimidic acid, ethyl ester, hydrochloride (1:1) → ethyl 2-methyl-1H-benzimidazole-4-carboxylate

HRID 1723109Notes

Reaction equation

HRID 1723109 reaction equation
[NH2:1][C:2]1[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[C:15](=N)(OCC)[CH3:16]>C(O)C>[CH3:15][C:16]1[NH:13][C:12]2[CH:11]=[CH:10][CH:9]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 11171330Ethyl 2,3-diaminobenzoate

Product 1

HCID 18680979ethyl 2-methyl-1H-benzimidazole-4-carboxylateYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(a-1) A mixture of 17 parts of ethyl 2,3-diaminobenzoate, 14 parts of ethyl ethanimidate hydrochloride and 240 parts of ethanol was stirred for 19 hours at reflux temperature. After evaporation, the residue was taken up in a potassium carbonate solution 10% and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated, yielding 19 parts (98.6%) of ehtyl 2-methyl-1H-benzimidazole-4-carboxylate as a residue (int. 65).

Workup

  1. temperatureat reflux temperature
  2. customAfter evaporation
  3. extractionthe product was extracted with trichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-47f397481fdb4fb9b3e07ad3ef20faba
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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