Methyl iodide → HCID 68445603, compound

HRID 1505801Notes

Reaction equation

HRID 1505801 reaction equation
[SH:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]=2[N:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C>[CH3:15][S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178497595HCID 178497595, compound

Product 1

HCID 68445603HCID 68445603, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-sulfanyl-1H-benzimidazole-4-carboxylate (prepared as described in WO2003/106430) (1.0 g) in DMF (15 mL), were added potassium carbonate (700 mg) and methyl iodide (0.32 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified on column chromatography to obtain the titled compound (860 mg) as white powder.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-73b8555cf5c54b70b7d9843cbbad5fa3
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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