Potassium Carbonate → 2-(4-Chlorophenyl)-4-[[(2-chlorophenyl)thio)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

HRID 1353008Notes

Reaction equation

HRID 1353008 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[SH:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:5]2[N:6]([C:8]3[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:10][CH:9]=3)[CH:7]=[C:3]([CH2:2][S:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[Cl:25])[N:4]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80599o-ChlorothiophenolHCID 108098434-chloromethyl-2-(4-chlorophenyl)-1-(4-(methylsulfonyl)phenyl]-1H-imidazole

Product 1

HCID 229979502-(4-Chlorophenyl)-4-[[(2-chlorophenyl)thio)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazoleYield 45.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloromethyl-2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole (Example 159, Step 1) (250 mg, 0.656 mmol) and 2-chlorothiophenol (190 mg, 1.31 mmol) in 5 ml of dimethylformamide was added potassium carbonate (226 mg, 1.64 mmol). The mixture was stirred rapidly overnight at room temperature and partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, the combined organic extracts were washed with brine, and dried-over sodium sulfate. The solution was filtered and then concentrated. Chromatography of the residue over silica gel using 50% ethyl acetate in hexane as the eluent followed by crystallization gave the title compound as a pure white crystalline solid (147 mg): mp (DSC) 153° C. Anal. Calc'd. for C23H18Cl2N2O2S2 (MW 489.44): C, 56.44; H, 3.71; N, 5.72. Found: C, 56.51; H, 3.54; N, 5.57.

Workup

  1. custompartitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customChromatography of the residue over silica gel using 50% ethyl acetate in hexane as the eluent followed by crystallization

Sources & evidence

ORD record
ord-a730b0fab2dc4d6aaf432d86c48c61d0
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

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