Methyl iodide → ethyl 2-methylthio-1H-benzimidazole-4-carboxylate

HRID 429665Notes

Reaction equation

HRID 429665 reaction equation
[SH:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]=2[N:3]=1.IC.[C:18](=O)([O-])[O-].[K+].[K+]>O>[CH3:18][S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178468777HCID 178468777, compound

Product 1

HCID 18354852ethyl 2-methylthio-1H-benzimidazole-4-carboxylateYield 58.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-mercapto-1H-benzimidazole-4-carboxylate (500 mg) were added iodomethane (351 mg) and potassium carbonate (622 mg) at ambient temperature and the mixture was stirred for 20 hours at same temperature. The reaction mixture was poured into water and extracted with chloroform. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with diisopropyl ether to give ethyl 2-methylthio-1H-benzimidazole-4-carboxylate (310 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-ecb41792b3824a0da1ea50e7b673cfdf
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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