Sodium methanesulfonate → 1-(2-Methanesulfonyl-thiazol-5-yl)-propan-1-one

HRID 1423040

Reaktionsgleichung

Reaktionsgleichung von HRID 1423040
Br[C:2]1[S:3][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:5][N:6]=1.[CH3:11][S:12]([O-])(=[O:14])=[O:13].[Na+]>CS(C)=O.CCOC(C)=O.[Cu]I>[CH3:11][S:12]([C:2]1[S:3][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:5][N:6]=1)(=[O:14])=[O:13]

Komponenten

6

Edukt 2

HCID 638112Sodium methanesulfonateHCID 592780851-(2-Bromothiazol-5-yl)propan-1-one

Produkt 1

HCID 592783971-(2-Methanesulfonyl-thiazol-5-yl)-propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 1-(2-bromo-thiazol-5-yl)-propan-1-one (75 mg, 0.34 mmol) in DMSO (3 mL) is added sodium methanesulfonate (41 mg, 0.34 mmol) followed by copper (I) iodide (65 mg, 0.34 mmol). The mixture is warmed in a microwave reactor at 120° C. After 1 hour, the reaction is diluted with EtOAc (20 mL) and washed with saturated aqueous sodium bicarbonate (50 mL) and brine (10 mL). The aqueous phase is extracted with EtOAc (2×10 mL). The combined organic layers are dried over magnesium sulfate, filtered and concentrated to afford 1-(2-methanesulfonyl-thiazol-5-yl)-propan-1-one which is used without further purification.

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate (50 mL) and brine (10 mL)
  2. extractionThe aqueous phase is extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-744a587cad594eac8fb372a0d157d933
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927550B2

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