Hydrochloric Acid → HCID 86644417, compound

HRID 2194710Notes

Reaction equation

HRID 2194710 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=1.C(N(CC)CC)C.Cl>CS(C)=O>[CH:2]([C:3]1[CH:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=1)=[O:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 68410437HCID 68410437, compound

Product 1

HCID 86644417HCID 86644417, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-[3-(Hydroxymethyl)-1-phenyl-1H-pyrazol-5-yl]benzenesulfonamide (379 mg) and triethylamine (1 mL) were dissolved in dimethyl sulfoxide (5 mL), and sulfur trioxide•pyridine complex (549 mg) was added at room temperature. After stirring at room temperature for 18 hr, 1 mol/L hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate, and the combined extracts were washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:3) to give the title compound as a pale-yellow oil (yield 331 mg, yield 88%).

Workup

  1. additionsulfur trioxide•pyridine complex (549 mg) was added at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe aqueous layer was extracted again with ethyl acetate
  4. washthe combined extracts were washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:3)

Sources & evidence

ORD record
ord-5fb2551a95bc479098dbaf97c8d187be
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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