Triethylamine → 2-(chloromethyl)-1-(methylsulfonyl)-1h-benzimidazole

HRID 1072005Notes

Reaction equation

HRID 1072005 reaction equation
[Cl:1][CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[N:4]([S:13]([CH3:12])(=[O:15])=[O:14])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 785712-Chloromethylbenzimidazole

Product 1

HCID 2656732-(chloromethyl)-1-(methylsulfonyl)-1h-benzimidazoleYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(chloromethyl)benzimidazole (80 g, 0.48 mol) and methanesulfonyl chloride (58.3 mL, 0.75 mol) in 0.5 L of methylene chloride, triethylamine (136 mL, 0.97 mol) was added dropwise under nitrogen. The resulting mixture was stirred at room temperature for 6 hours. The mixture was filtered and the filtrate was evaporated. The residue was triturated in methanol and filtered to afford 74.9 g of the title compound as a brown solid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was triturated in methanol
  4. filtrationfiltered

Sources & evidence

ORD record
ord-dbba3128943e4d57ad430e63766d3b56
Source dataset
uspto-grants-2005_06
Patent number
US06908936B2

Reaction notes

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