HCID 21090548, Verbindung → 4-[[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-3-methyl-pyrazol-4-yl]methyl]pyridine

HRID 350882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350882
[P](I)(I)(I)I.[Cl:6][C:7]1[CH:8]=[C:9]([S:14][C:15]2[N:19]([CH:20]([CH3:22])[CH3:21])[N:18]=[C:17]([CH3:23])[C:16]=2[C:24]2C=CN=C(C)[C:25]=2O)[CH:10]=[C:11]([Cl:13])[CH:12]=1.S(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[Cl:6][C:7]1[CH:8]=[C:9]([S:14][C:15]2[N:19]([CH:20]([CH3:21])[CH3:22])[N:18]=[C:17]([CH3:23])[C:16]=2[CH2:24][C:25]2[CH:21]=[CH:20][N:19]=[CH:15][CH:16]=2)[CH:10]=[C:11]([Cl:13])[CH:12]=1

Komponenten

5

Edukt 3

HCID 21090548HCID 21090548, VerbindungHCID 23665763Sodium BisulfiteHCID 178506614HCID 178506614, Verbindung

Produkt 1

HCID 99085114-[[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-3-methyl-pyrazol-4-yl]methyl]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 466 mg of phosphorus tetraiodide in 15 mL of benzene was heated at 80° C. for 15 minutes. To this solution was added dropwise a solution of 400 mg of 4-[[5-(3,5-dichloro-phenylsulfanyl)-1-isopropyl-3-methyl-1H-pyrazol-4-yl]-hydroxy-methyl-pyridine in 10 mL of benzene. The mixture was then heated at 80° C. for 1 hour then allowed to cool to room temperature. Then 8 mL of 10% aqueous sodium bisulphite solution was added and the biphasic mixture stirred for 1 hour. The aqueous phase was extracted three times with 30 mL of ethyl acetate and combined extracts were washed with brine, dried, filtered and evaporated to give a yellow residue which was purified by flash chromatography on silica gel using ethyl acetate/hexane (1:1 then 2:1) for the elution to give 238 mg of 4-[5-(3,5-dichloro-phenylsulfanyl)-1-isopropyl-3-methyl-1H-pyrazol-4-ylmethyl]-pyridine as a white solid. Mass spectrum (ES) m/z 392 [M+H]+, 433 [M+H+MeCN]+.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionThe aqueous phase was extracted three times with 30 mL of ethyl acetate
  3. washwere washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow residue which
  8. customwas purified by flash chromatography on silica gel
  9. wash2:1) for the elution

Quellen und Nachweise

ORD-Eintrag
ord-90e498629e504fe0a54ccfd8b36e363c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183296B2

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