Methyl iodide → 1H-Benzimidazole, 5,6-dichloro-1-methyl-2-(methylthio)-

HRID 725722Notes

Reaction equation

HRID 725722 reaction equation
Cl[C:2]1C(Cl)=CC2N=C(S)NC=2C=1.[OH-].[K+].IC.[Cl:17][C:18]1[C:28]([Cl:29])=[CH:27][C:21]2[N:22]=[C:23]([S:25][CH3:26])[NH:24][C:20]=2[CH:19]=1>C(O)C>[Cl:17][C:18]1[C:28]([Cl:29])=[CH:27][C:21]2[N:22]=[C:23]([S:25][CH3:26])[N:24]([CH3:2])[C:20]=2[CH:19]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 6081045,6-dichloro-2-(methylthio)-1H-benzo[d]imidazoleHCID 178527798HCID 178527798, compound

Product 1

HCID 103772851H-Benzimidazole, 5,6-dichloro-1-methyl-2-(methylthio)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5,6-dichloro-2-mercaptobenzimidazole (8.76 g, 0.04 mol) in 50 ml 95% ethanol was treated with 10 ml of 45% aqueous potassium hydroxide to give a solution. Iodomethane (7 ml, 0.096 mol) was added. The reaction mixture was refluxed for two hours. Cooling overnight yielded precipitant, which was filtered, water-washed, and dried to yield 5.61 g, mp 115° C. The reaction filtrate was rotary evaporated and the residue reslurried in water. After filtration and drying, an additional 3.52 g was obtained, mp 110° C. NMR analysis indicated the presence of some 5,6-DiChloro-2-(methylthio)benzimidazole as an impurity.

Workup

  1. customto give a solution
  2. temperatureThe reaction mixture was refluxed for two hours
  3. temperatureCooling overnight
  4. customyielded precipitant
  5. filtrationwhich was filtered
  6. washwater-washed
  7. customdried
  8. customto yield 5.61 g, mp 115° C
  9. customThe reaction filtrate was rotary evaporated
  10. filtrationAfter filtration
  11. customdrying
  12. customan additional 3.52 g was obtained

Sources & evidence

ORD record
ord-4e0dbb5bdff64281b479e1d64fcb5768
Source dataset
uspto-grants-1998_01
Patent number
US05707794

Reaction notes

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