Hydrochloric Acid → Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethylamino-benzimidazole-7-carboxylate

HRID 277462Notes

Reaction equation

HRID 277462 reaction equation
CI.[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19]2[C:29]([NH:30][C:31]([NH:33][CH2:34][CH3:35])=S)=[CH:28][CH:27]=[CH:26][C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13][CH:12]=1)#[N:4].Cl>C(O)C>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:19]3[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=[CH:28][C:29]=3[N:30]=[C:31]2[NH:33][CH2:34][CH3:35])=[CH:13][CH:12]=1)#[N:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 53943039Ethyl 2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-(ethylthioureido)benzoate

Product 1

HCID 22596759Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethylamino-benzimidazole-7-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl iodide (4.5 g) was added to a solution of ethyl 2-[[(2′-cyanobiphenyl-4-yl)methyl]amino]-3-(ethylthioureido)benzoate (1.8 g) in ethanol (50 ml), and the mixture was heated under reflux for 12 hours. To the reaction mixture was added 1N-HCl (60 ml) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated to dryness and the concentrate was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogen carbonate and water and dried. The solvent was evaporated to dryness and the residue was purified by column chromatography on silica gel to afford yellow syrup (0.96 g, 58%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutionthe concentrate was dissolved in ethyl acetate
  5. washThe solution was washed with an aqueous solution of sodium hydrogen carbonate and water
  6. customdried
  7. customThe solvent was evaporated to dryness
  8. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a18948c5c8004b78957299668eb60b86
Source dataset
uspto-grants-2002_03
Patent number
US06355808B2

Reaction notes

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