Trifluoromethylsulfinylchloride → 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile

HRID 1429000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429000
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[CH:3]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.CNC.[C:35]([S:39](Cl)=[O:40])([F:38])([F:37])[F:36]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:39]([C:35]([F:38])([F:37])[F:36])=[O:40]

Komponenten

5

Edukt 3

HCID 11008121TrifluoromethylsulfinylchlorideHCID 12199009Dimethylamine p-toluenesulfonateHCID 684093715-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)-phenyl)-1H-pyrazole-3-carbonitrile

Produkt 1

HCID 898587905-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrileAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile (140 g, 459.6 mmol, 1.00 eq.) and dimethylamine tosylate (151.8 g, 698.6 mmol, 1.52 eq.) in toluene (840 mL) was added CF3SOCl (89.7 g, 588.3 mmol, 1.28 eq.). After the mixture was stirred at 40° C. for 16 h, nitrogen was bubbled through the solution and the solution was cooled to rt. Then the mixture was poured into 2 L ice/water and stirred at 0° C. for 1 h. The precipitated solid was isolated by filtration and dried under vacuum. The solid was recrystallized with toluene to give 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile (125 g, 64%) as yellow solid.

Aufarbeitung

  1. customnitrogen was bubbled through the solution
  2. temperaturethe solution was cooled to rt
  3. additionThen the mixture was poured into 2 L ice/water
  4. stirringstirred at 0° C. for 1 h
  5. customThe precipitated solid was isolated by filtration
  6. customdried under vacuum
  7. customThe solid was recrystallized with toluene

Quellen und Nachweise

ORD-Eintrag
ord-574084f2cfb3495da39d63f838e3a4f1
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937185B2

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