Dimethylformamide → 2-(4-Chlorophenyl)-4-[[(2,6-dichlorophenyl)thio]methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

HRID 1166396Notes

Reaction equation

HRID 1166396 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]=[C:28]([Cl:32])[C:27]=1[SH:33].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>>[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:33][C:27]3[C:26]([Cl:25])=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:32])[N:4]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 90671Benzenethiol, 2,6-dichloro-HCID 108098434-chloromethyl-2-(4-chlorophenyl)-1-(4-(methylsulfonyl)phenyl]-1H-imidazole

Product 1

HCID 229980272-(4-Chlorophenyl)-4-[[(2,6-dichlorophenyl)thio]methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

Procedure

To a solution of 4-chloromethyl-2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole (Example 159, Step 1) (250 mg, 0.656 mmole) and 2,6-dichlorothiophenol in 5 ml of dimethylformamide (235 mg, 1.31 mmol) was added 226 mg (1.64 mmol) of potassium carbonate. The resulting mixture was stirred rapidly at room temperature for two days. The mixture was partitioned between ethyl acetate and water and the aqueous layer was further extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using 50% ethyl acetate in hexane gave the title compound, 282 mg, as a pure white solid: mp (DSC) 202° C. Anal. Calc'd. for C23H17Cl3N2O2S2 (MW 523.89): C, 52.73; H, 3.27; N, 5.35. Found: C, 52.55; H, 2.98; N, 5.19.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous layer was further extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e158c31489d74c57a2e3c9c23e718ae5
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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