Methyl iodide → 2-(methylsulfanyl)-4,5,6,7-tetrahydro-1H-benzimidazole

HRID 1429986Notes

Reaction equation

HRID 1429986 reaction equation
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[SH:10].[C:11]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:11][S:10][C:2]1[NH:3][C:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:1]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1785278154,5,6,7-tetrahydro-1H-benzimidazole-2-thiol

Product 1

HCID 250219552-(methylsulfanyl)-4,5,6,7-tetrahydro-1H-benzimidazoleYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4,5,6,7-tetrahydro-1H-benzimidazole-2-thiol (500 mg) in acetone (5 mL) were added K2CO3 (1344 mg) and MeI (0.223 mL) at room temperature. After stirring for 1 h, the mixture was quenched with water, and extracted with ethyl acetate, and the extract was washed with brine and dried over magnesium sulfate. The residue was purified by column chromatography (silica gel, eluted with 40%-90% EtOAc in hexane) to give 2-(methylsulfanyl)-4,5,6,7-tetrahydro-1H-benzimidazole (545 mg) as a white solid.

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe residue was purified by column chromatography (silica gel, eluted with 40%-90% EtOAc in hexane)

Sources & evidence

ORD record
ord-a5e55b3938a741599fff66ca2011cf89
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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