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

HRID 559689

Reaktionsgleichung

Reaktionsgleichung von HRID 559689
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 dimethyl sulfoxide (3 mL) was added the sodium methanesulfonate (41 mg, 0.34 mmol) followed by copper (I) iodide (65 mg, 0.34 mmol). The mixture was heated in a microwave at 120° C. for 1 hour. The reaction was diluted with EtOAc (20 mL) and washed with saturated aqueous sodium bicarbonate solution (50 mL) and brine (10 mL). The aqueous phase was extracted with EtOAc (2×10 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to afford 1-(2-methanesulfonyl-thiazol-5-yl)-propan-1-one which was used without further purification.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6f99707be40f431398e8751b27a911c5
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063065B2

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