Water → 4-(4-chloro-benzylsulfanyl)-3,5-dimethyl-1H-pyrazole

HRID 1410382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410382
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][S:7][CH:8]([C:12](=O)[CH3:13])[C:9](=O)[CH3:10])=[CH:4][CH:3]=1.O.[NH2:18][NH2:19].O>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][S:7][C:8]2[C:12]([CH3:13])=[N:18][NH:19][C:9]=2[CH3:10])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 221748613-(4-Chloro-benzylsulfanyl)-pentane-2,4-dione

Produkt 1

HCID 221748524-(4-chloro-benzylsulfanyl)-3,5-dimethyl-1H-pyrazoleAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of crude 3-(4-chloro-benzylsulfanyl)-pentane-2,4-dione [prepared as described above from 3-chloro-pentan-2,3-dione (1.03 g, 7.63 mmol) and 4-chlorobenzyl mercaptan (1.21 g, 7.63 mmol)] in ethanol (60 mL) was added hydrazine hydrate (0.713 mL, 22.9 mmol) and p-toluenesulfonic acid monohydrate (ca. 25 mg). The solution was heated to reflux and stirred for 15 hours. The reaction mixture was allowed to cool to room temperature, and water (300 mL) was added. The precipitate that formed was removed by filtration, washed with water, and dried to provide 1.38 g (72%) of the product as a white solid: 1H NMR (CDCl3) δ 7.17 (d, J=8.4 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 3.57 (s, 2H), and 2.02 (s, 6H) ppm. 13C NMR (CDCl3) δ 137.2, 132.7, 130.3, 128.3, 105.2, 39.9, 10.7 ppm.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. customThe precipitate that formed
  4. customwas removed by filtration
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e4fec1d6d6e342ea9aa6735f4981345d
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921547B2

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