p-Toluenesulfonic acid monohydrate → 2-(Chloromethyl)-1-phenyl-1H-benzimidazole

HRID 1284481

Reaction equation

HRID 1284481 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[Cl:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 14819969N-(2-Anilinophenyl)-2-chloroacetamide

Product 1

HCID 202518962-(Chloromethyl)-1-phenyl-1H-benzimidazoleYield 36.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-chloro-N-(2-anilinophenyl)acetamide (10 g) and p-toluenesulfonic acid monohydrate (4.5 g) in benzene (250 ml) was refluxed for 1.5 hours under an azeotropic dehydration. After being cooled to ambient temperature, the reaction mixture was diluted with an aqueous sodium bicarbonate solution and extracted with ethyl acetate three times. The combined organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel (100 g) with dichloromethane as an eluent to afford 2-chloromethyl-1-phenyl-1H-benzimidazole (3.4 g).

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic layer was washed successively with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residual oil was purified by column chromatography on silica gel (100 g) with dichloromethane as an eluent

Sources & evidence

ORD record
ord-5720073835484745bf2c062210db3bc8
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Linked notes

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