Thionyl Chloride → 5-Amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-4-trifluoromethylsulfenylpyrazole

HRID 1871567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1871567
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[Cl:16])[C:12]([F:18])([F:17])[O:11][C:10]3([F:20])[F:19])[N:5]=[CH:4][CH:3]=1.[F:21][C:22]([F:27])([F:26])[S:23]([O-])=O.[Na+].S(C1C=CC(C)=CC=1)(O)(=O)=O.CNC.S(Cl)(Cl)=O>C1(C)C=CC=CC=1.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[Cl:16])[C:12]([F:18])([F:17])[O:11][C:10]3([F:20])[F:19])[N:5]=[CH:4][C:3]=1[S:23][C:22]([F:27])([F:26])[F:21]

Komponenten

7

Edukt 4

HCID 24386Thionyl ChlorideHCID 12199009Dimethylamine p-toluenesulfonateHCID 186915105-Amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)pyrazoleHCID 23690734Sodium trifluoromethanesulfinate

Produkt 1

HCID 186915325-Amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-4-trifluoromethylsulfenylpyrazoleAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a suspension wherein 5-amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)pyrazole (391 mg, 1.27 mmol), sodium trifluromethanesulfinate (397 mg, 2.54 mmol) and dimethylamine tosylate (690 mg, 3.17 mmol) are in toluene (4 ml), thionyl chloride (302 mg, 2.54 mmol) was added dropwise under ice cooling over a period of about 10 minutes and then stirred under heating at 50 to 60° C. for 14 hours. After allowing to cool, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to give 200 mg of 5-amino-1-(6-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-4-trifluoromethylsulfenylpyrazole.

Aufarbeitung

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-180381f3d4aa4e70b4c250ade5eca81e
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06103750

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