4-(Methylsulfonyl)phenylhydrazine hydrochloride → 6-methoxy-2-[1-(4-methylsulfonylphenyl)-3-trifluoromethyl-1H-pyrazol-5-yl]benzothiazole

HRID 369080

Reaktionsgleichung

Reaktionsgleichung von HRID 369080
[F:1][C:2]([F:20])([F:19])[C:3](=O)[CH2:4][C:5]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)=O.Cl.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][NH2:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>C(O)C>[CH3:17][O:16][C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([C:5]3[N:32]([C:29]4[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:31][CH:30]=4)[N:33]=[C:3]([C:2]([F:20])([F:19])[F:1])[CH:4]=3)[S:8][C:9]=2[CH:15]=1

Komponenten

4

Edukt 2

HCID 27351814-(Methylsulfonyl)phenylhydrazine hydrochlorideHCID 154910984,4,4-Trifluoro-1-(6-methoxybenzothiazol-2-yl)butane-1,3-dione

Produkt 1

HCID 154910956-methoxy-2-[1-(4-methylsulfonylphenyl)-3-trifluoromethyl-1H-pyrazol-5-yl]benzothiazoleAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The mixture of 4,4,4-trifluoro-1-(6-methoxybenzothiazol-2-yl)butane-1,3-dione (300 mg, 1.0 mmol) and 4-methylsulfonyl-phenylhydrazine hydrochloride (260 mg, 1.1 mmol) was heated under reflux in ethanol (50 ml) for 3.5 hours, and then allowed to cool. The precipitated crystals were collected and subjected to recrystallization from ethanol and ethyl acetate-isooctane to afford 6-methoxy-2-[1-(4-methylsulfonylphenyl)-3-trifluoromethyl-1H-pyrazol-5-yl]benzothiazole (350 mg, 77%). NMR(CDCl3) δ: 3.11 (3H, s), 3.89 (3H, s), 7.11 (1H, dd, J=2.3 Hz, 8.6 Hz), 7.20 (1H, s), 7.32 (1H, d, J=2.3 Hz), 7.75 (2H, d, J=8.6 Hz), 7.82 (1H, d, J=8.6 Hz), 8.04 (2H, d, J=8.6 Hz); mp 217-218° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto cool
  3. customThe precipitated crystals were collected
  4. customsubjected to recrystallization from ethanol and ethyl acetate-isooctane

Quellen und Nachweise

ORD-Eintrag
ord-5c378cd8b0e74335b069ebce25e52dd4
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136831

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