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

HRID 340766Notes

Reaction equation

HRID 340766 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. The reaction was stirred at rt overnight, then the volatiles were removed and the residue was partitioned between EtOAc and water. Concentration of the EtOAc layer afforded the desired product as a white foam, which was used in the next step without further purification.

Workup

  1. stirringThe reaction was stirred at rt overnight
  2. customthe volatiles were removed
  3. customthe residue was partitioned between EtOAc and water

Sources & evidence

ORD record
ord-813520244f8f4eb3825465972b17b708
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

Loading…