4-Toluenesulfonyl chloride → 4-Propionylpyridine oxime tosylate

HRID 371400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 371400
[C:1](=[N:10][OH:11])([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)([OH:11])(=[O:20])=[O:19].[C:1](=[N:10][OH:11])([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 1363417421-(Pyridin-4-yl)propan-1-one oxime

Produkt 1

HCID 1363872634-Propionylpyridine oxime tosylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To the oxime 2 of Example 2 (5.0 g, 33 mmol) dissolved in pyridine (31 mL) was added p-toluenesulfonyl chloride (7.4 g, 39 mmol) and the reaction mixture stirred at room temperature for 24 hours. Pyridine hydrochloride was removed by filtration and the filtrate concentrated under reduced pressure. The solid obtained was slurried in hexanes, filtered, and air dried to give the compound 3 as a pale peach-colored solid: NMR (CDCl3) δ 1.12 (t, 3H, J=8 Hz), 2.45 (s, 3H), 2.81 (q, 2H, J=8 Hz), and 7.27-7.98 (m, 8H).

Aufarbeitung

  1. customPyridine hydrochloride was removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe solid obtained
  4. filtrationfiltered
  5. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-f2d87eba931649f592dc6d67dec8dc33
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04532250

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