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(E)-N-[4-(1,3-benzodioxol-5-yl)-1-benzyl-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethenesulfonamide → N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethanesulfonamide

HRID 1062811
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Reaktionsgleichung

Reaktionsgleichung von HRID 1062811
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:34][CH3:35])=[N:12][N:13](CC4C=CC=CC=4)[C:14]=3[NH:15][S:16](/[CH:19]=[CH:20]/[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1.[H][H]>C(O)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:34][CH3:35])=[N:12][NH:13][C:14]=3[NH:15][S:16]([CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1
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Komponenten

4

Edukt 2

HCID 22282047(E)-N-[4-(1,3-benzodioxol-5-yl)-1-benzyl-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethenesulfonamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22281999N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethanesulfonamideAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

(E)-N-[4-(1,3-benzodioxol-5-yl)-1-benzyl-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethenesulfonamide (1.2 g) (Preparation 57) was dissolved in acetic acid (50 ml). Under an atmosphere of nitrogen, Pearlmann's catalyst (JM type 91, 200 mg) was added and the reaction was stirred for 24 h under 2 bars of hydrogen at 50C. The reaction mixture was filtered on a short pad of Celite® and concentrated under reduced pressure. To the oily residue was added water (dichloromethane (200 ml). The phases were separated, the organic phase washed with a 10% aqueous solution of sodium bicarbonate (2×100 ml). The aqueous phase was then extracted with dichloromethane (2×10 ml), the combined organic fractions were dried over sodium sulfate and concentrated under reduced pressure to yield the title compound as a colourless oil (0.96 g).

Aufarbeitung

  1. additionUnder an atmosphere of nitrogen, Pearlmann's catalyst (JM type 91, 200 mg) was added
  2. filtrationThe reaction mixture was filtered on a short pad of Celite®
  3. concentrationconcentrated under reduced pressure
  4. additionTo the oily residue was added water (dichloromethane (200 ml)
  5. customThe phases were separated
  6. washthe organic phase washed with a 10% aqueous solution of sodium bicarbonate (2×100 ml)
  7. extractionThe aqueous phase was then extracted with dichloromethane (2×10 ml)
  8. dry with materialthe combined organic fractions were dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e90c73a7da1f45309cd6ec4deebe2370
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06962923B2

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