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Hydrochloric Acid → HCID 86644417, Verbindung

HRID 2194710
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2194710
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 68410437HCID 68410437, Verbindung

Produkt 1

HCID 86644417HCID 86644417, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5fb2551a95bc479098dbaf97c8d187be
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08334301B2

Notizen zur Reaktion

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