Cesium carbonate → 4-(4-iodo-1H-pyrazol-1-yl)tetrahydro-2H-thiopyran 1,1-dioxide

HRID 1485766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485766
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.CS(O[CH:12]1[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)([O-])C.[K+]>CN(C=O)C.O>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH:12]2[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]2)[CH:6]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 770224-IodopyrazoleHCID 23665647Potassium tert-butoxideHCID 898088401,1-dioxidotetrahydro-2H-thiopyran-4-yl methanesulfonate

Produkt 1

HCID 1180801974-(4-iodo-1H-pyrazol-1-yl)tetrahydro-2H-thiopyran 1,1-dioxideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 4-iodo-1H-pyrazole (1.00 g, 5.16 mmol), 1,1-dioxidotetrahydro-2H-thiopyran-4-yl methanesulfonate (1.77 g, 7.73 mmol) and cesium carbonate (2.52 g, 7.73 mmol) in DMF (10 mL) was heated to 80° C. for 2 h. The reaction was cooled to room temperature, and potassium tert-butoxide (0.578 g, 5.16 mmol) was added. The reaction mixture stirred at room temperature for 30 minutes and then water (30 mL) was added. The mixture stirred for 4 h and was then filtered. The filter cake was washed with water (10 mL) and dried in vacuo to afford 4-(4-iodo-1H-pyrazol-1-yl)tetrahydro-2H-thiopyran 1,1-dioxide (1.00 g, 60%) as an off-white solid. MS (ESI, pos. ion) m/z 327 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. stirringThe mixture stirred for 4 h
  3. filtrationwas then filtered
  4. washThe filter cake was washed with water (10 mL)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-63614126339b457ab75f9304577a61f0
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422281B2

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