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

HRID 1698188ノート

反応式

HRID 1698188 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fc96560b06e24b85a3800b5ed6c3a224
出典データセット
uspto-grants-2012_04
特許番号
US08163918B2

反応ノート

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