Hydrochloric Acid → 4-[5-(4-Fluorophenyl)-2-trifluoromethyl-1H-imidazol-4-yl]benzenesulfonamide

HRID 2231108Notes

Reaction equation

HRID 2231108 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](COCC[Si](C)(C)C)[C:11]([C:21]([F:24])([F:23])[F:22])=[N:10][C:9]=2[C:25]2[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.Cl>CCO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:21]([F:23])([F:22])[F:24])=[N:10][C:9]=2[C:25]2[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 184637044-[5-(4-fluorophenyl)-2-trifluoromethyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-4-yl]benzenesulfonamide

Product 1

HCID 184636334-[5-(4-Fluorophenyl)-2-trifluoromethyl-1H-imidazol-4-yl]benzenesulfonamideYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of protected sulfonamide from step 2 (500 mg, 1 mmol) in a solution of 3 N HCl (5 ml) in EtOH (4 ml) was heated to reflux for 1 hour, cooled and diluted with water (20 ml). The resulting mixture was extracted with methylene chloride, dried (Na2SO4) and the solvent was evaporated. The residue was recrystallized from toluene containing a small amount of ethyl acetate to give the title product (150 mg, 40%): m.p. 259-260° C. Anal. Calc'd. for C16H11N3O2F4S: C, 49.87; H, 2.88; N, 10.90; S, 8.32. Found: C, 50.30; H, 3.10; N, 10.55; S, 8.73.

Workup

  1. temperatureto reflux for 1 hour
  2. temperaturecooled
  3. extractionThe resulting mixture was extracted with methylene chloride
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated
  6. customThe residue was recrystallized from toluene containing a small amount of ethyl acetate

Sources & evidence

ORD record
ord-d143ab0df4b347ccbd93285c1a7fca58
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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