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

HRID 1361187

Reaction equation

HRID 1361187 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8357b378d7ea48b29f826b117a82ae3c
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Linked notes

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