Water → 1-(2-Chloroethyl)-1H-benzimidazole

HRID 2231232Notes

Reaction equation

HRID 2231232 reaction equation
O[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1.S(Cl)([Cl:15])=O.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:15][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 2281312-(1H-Benzimidazol-1-yl)ethan-1-olHCID 516892Sodium Bicarbonate

Product 1

HCID 5831471-(2-Chloroethyl)-1H-benzimidazoleYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of 30 g (0.185 mole) of 1-(2-hydroxyethyl)benzimidazole in 200 ml of methylene chloride was added dropwise 13.5 ml (0.185 mole) of thionyl chloride in 50 ml of the same solvent. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was added to an equal volume of water and made basic (pH 8-9) by the addition of sodium bicarbonate. The organic phase was separated, dried over magnesium sulfate and evaporated to give 27.3 g of product.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-48dedf1c822e4d4d9ee4e9ab61855b7a
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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