Sodium Sulfite → (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-[(methylsulfonyl)methyl]phenyl)acrylamide

HRID 30727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30727
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25]SC)=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.Cl[C:29]1C=CC=C(C(OO)=O)C=1.[S:39]([O-:42])([O-])=[O:40].[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][S:39]([CH3:29])(=[O:42])=[O:40])=[CH:23][CH:24]=2)=[O:17])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 69210621(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(methylthio)methyl]phenyl}acrylamide

Produkt 1

HCID 10047367(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-[(methylsulfonyl)methyl]phenyl)acrylamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(methylthio)methyl]phenyl}acrylamide (600 mg), m-chloroperbenzoic acid (780 mg) and tetrahydrofuran (50 mL) was stirred at 0° C. for 20 min. A saturated aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was further stirred for 10 min. and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate, and then with saturated brine, dried (MgSO4) and concentrated. The obtained solid was recrystallized from acetone-hexane to give (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-[(methylsulfonyl) methyl]phenyl)acrylamide (490 mg, yield 75%) as colorless prism crystals. melting point: 251-252° C.

Aufarbeitung

  1. stirringthe mixture was further stirred for 10 min.
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialwith saturated brine, dried (MgSO4)
  5. concentrationconcentrated
  6. customThe obtained solid was recrystallized from acetone-hexane

Quellen und Nachweise

ORD-Eintrag
ord-84d27d96890147c68d709c8dcc2a656c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423159B2

Notizen zur Reaktion

Wird geladen…