S-Benzylthiuronium chloride → 2-Benzylthio-5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-1H-imidazole

HRID 2231099Notes

Reaction equation

HRID 2231099 reaction equation
Cl.[CH2:2]([S:9][C:10](=[NH:12])[NH2:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH:21]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)Br)=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>CCO>[CH2:2]([S:9][C:10]1[NH:11][C:20]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)=[C:21]([C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=2)[N:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10852S-Benzylthiuronium chlorideHCID 516892Sodium BicarbonateHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 184637522-Benzylthio-5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-1H-imidazoleYield 17.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of S-benzylisothiourea hydrochloride (300 mg, 1.5 mmol), 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)-2-bromoethan-1-one (Example 1, Method B, step 1) (500 mg, 1.3 mmol) and NaHCO3 (500 mg, 6 mmol) in EtOH (10 ml) was heated to reflux for 3 hours. After evaporation of the solvent, the residue was treated with water (25 ml) and extracted with methylene chloride (25 ml). After drying (MgSO4), the organic phase was evaporated. The residue was purified by chromatography on silica gel, eluting with ethyl acetate/toluene (25/75). The crude material was recrystallized from toluene and hexane to give 100 mg (17%) of titled product: m.p. 155-156° C. Anal. Calc'd. for C23H19FN2O2S2: C, 62.99; H, 4.37; N, 6.39; S, 14.62. Found: C, 62.93; H, 4.41; N, 5.98; S, 14.33.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. customAfter evaporation of the solvent
  4. additionthe residue was treated with water (25 ml)
  5. extractionextracted with methylene chloride (25 ml)
  6. dry with materialAfter drying (MgSO4)
  7. customthe organic phase was evaporated
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with ethyl acetate/toluene (25/75)
  10. customThe crude material was recrystallized from toluene and hexane

Sources & evidence

ORD record
ord-3f9bda7cc9b042728f8eb95bf598ffcd
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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