Benzenesulfonyl chloride → 2-(4-Chlorophenyl)-1-(phenylsulfonyl)-1H-imidazole

HRID 63232Notes

Reaction equation

HRID 63232 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:23])=[O:22])[CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 2429482-(4-chlorophenyl)-1H-imidazole

Product 1

HCID 497885002-(4-Chlorophenyl)-1-(phenylsulfonyl)-1H-imidazoleYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-chlorophenyl)-1H-imidazole (9f) (20 mmol) in anhydrous THF (200 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 1.2 g, 30 mmol) and stirred for 30 min. Benzenesulfonyl chloride (2.82 mL, 22 mmol) was added and the reaction mixture was stirred overnight. After dilution by 100 mL of saturated NaHCO3 solution (aqueous), the reaction mixture was extracted by ethyl acetate (500 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (hexane:ethyl acetate 2:1) to give a pale solid. Yield: 54.9%. 1H NMR (500 MHz, CDCl3) δ 7.65 (d, J=2.0 Hz, 1H), 7.58 (t, J=7.5 Hz, 1H), 7.43 (d, J=8.5 Hz, 2H), 7.38 (t, J=8.0 Hz, 2H), 7.34-7.36 (m, 4H), 7.12 (d, J=1.5 Hz, 1H). MS (ESI): calculated for C15H11ClN2O2S, 318.0. found 341.0 [M+Na]+.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. extractionAfter dilution by 100 mL of saturated NaHCO3 solution (aqueous), the reaction mixture was extracted by ethyl acetate (500 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (hexane:ethyl acetate 2:1)
  6. customto give a pale solid

Sources & evidence

ORD record
ord-1ccdfc20f5b0481f91eb4c6f13285232
Source dataset
uspto-grants-2016_09
Patent number
US09447049B2

Reaction notes

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