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

HRID 1423040ノート

反応式

HRID 1423040 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 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.

後処理

  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

出典と根拠

ORDレコード
ord-744a587cad594eac8fb372a0d157d933
出典データセット
uspto-grants-2015_01
特許番号
US08927550B2

反応ノート

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