Imidazole → 1-(Phenylsulfonyl)-1H-imidazole

HRID 370650Notes

Reaction equation

HRID 370650 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:6]1([S:12](Cl)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCCC1>[C:6]1([S:12]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 7369Benzenesulfonyl chloride

Product 1

HCID 5552261-(Phenylsulfonyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of imidazole (27.2 g, 0.4 mol), and benzenesulphonyl chloride (35.3 g, 0.2 mol) in dry tetrahydrofuran (200 ml) was stirred at ambient temperature for 1 h, when the resulting precipitate was removed by filtration. The filtrate was evaporated under reduced pressure and the resulting solid was recrystallised from benzene/petroleum ether (b.p. 40°-60°), to afford 1-(benzenesulphonyl)imidazole, m.p. 82°-83°.

Workup

  1. customwhen the resulting precipitate was removed by filtration
  2. customThe filtrate was evaporated under reduced pressure
  3. customthe resulting solid was recrystallised from benzene/petroleum ether (b.p. 40°-60°)

Sources & evidence

ORD record
ord-5f2a4998f18b4102993b03b35cdc1ec2
Source dataset
uspto-grants-1985_07
Patent number
US04528195

Reaction notes

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