Thionyl Chloride → 1H-Benzimidazole, 2-(chloromethyl)-1-ethyl-

HRID 1884817Notes

Reaction equation

HRID 1884817 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12]O)[CH3:2].S(Cl)([Cl:16])=O>ClCCl>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12][Cl:16])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 799599(1-Ethyl-1H-benzimidazol-2-yl)methanol

Product 1

HCID 124084321H-Benzimidazole, 2-(chloromethyl)-1-ethyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

20 mg (0.11 mmol) 1-ethyl-2-hydroxymethylbenzimidazole was dissolved in 2 ml dichloromethane. Thionyl chloride (24 μl, 0.33 mmol) was diluted 20 times with dichloromethane and the solution was added to the reaction mixture. Reaction mixture was stirred at room temperature for two hours, evaporated to dryness and washed with water to yield 1-ethyl-2-chloromethylbenzimidazole as pale yellow crystals, 36 mg (95%).

Workup

  1. additionthe solution was added to the reaction mixture
  2. customReaction mixture
  3. customevaporated to dryness
  4. washwashed with water

Sources & evidence

ORD record
ord-1152884ff66147359d1c0759f8de633a
Source dataset
uspto-grants-2004_07
Patent number
US06767909B2

Reaction notes

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