Methyl iodide → 6-Chloro-5-iodo-2-(methylthio)-1H-benzo[d]imidazole

HRID 1960107Notes

Reaction equation

HRID 1960107 reaction equation
C([O-])([O-])=O.[K+].[K+].I[CH3:8].[Cl:9][C:10]1[C:19]([I:20])=[CH:18][C:13]2[NH:14][C:15](=[S:17])[NH:16][C:12]=2[CH:11]=1>CC(C)=O>[Cl:9][C:10]1[C:19]([I:20])=[CH:18][C:13]2[N:14]=[C:15]([S:17][CH3:8])[NH:16][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 574814685-Chloro-6-iodo-1H-benzo[d]imidazole-2(3H)-thione

Product 1

HCID 574814886-Chloro-5-iodo-2-(methylthio)-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (0.22 g, 1.61 mmol), followed by iodomethane (0.1 mL, 1.61 mmol), was added to a solution of 5-chloro-6-iodo-1,3-dihydro-2H-benzimidazole-2-thione (1 g, 3.22 mmol) in acetone (20 mL) at 0° C. The reaction was stirred at rt for 1 h. Additional K2CO3 (1.61 mmol) and iodomethane (1.61 mmol) were added, and stirring continued at rt overnight. Volatiles were removed and the residue was partitioned between EtOAc and water. Concentration afforded the desired product as a white foam, which was used in the next step without further purification.

Workup

  1. stirringstirring
  2. waitcontinued at rt overnight
  3. customVolatiles were removed
  4. customthe residue was partitioned between EtOAc and water
  5. concentrationConcentration

Sources & evidence

ORD record
ord-63029c3c2b7649c3b0c048f9fd5b42c1
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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