Triethylamine → 4-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide

HRID 1644715

反応式

HRID 1644715 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:21]([C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH:25]=[O:26])#[CH:22].C(OCC)(=O)C>C(#N)C.[Cu]I>[CH:25]([C:24]1[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=1[C:21]#[C:22][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1)=[O:26]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 128184-Bromo-N,N-dimethylbenzenesulphonamideHCID 6403682-Ethynylbenzaldehyde

生成物 1

HCID 593508554-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide収率 63%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-bromo-N,N-dimethylbenzenesulfonamide (610 mg, 2.31 mmol) bis(triphenylphosphine)palladium(II) chloride (Pd(PPh3)2Cl2) (33 mg, 0.05 mmol), copper (I) iodide (5 mg, 0.03 mmol) and triethylamine (3 mL) was degassed with argon. To the above mixture was added a degassed solution of 2-ethynyl-benzaldehyde (300 mg, 2.31 mmol) in acetonitrile (3 mL). The resulting mixture was heated at 80° C. for 3 hours under argon, and then cooled to room temperature, treated with ethyl acetate, and then washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 5-40% ethyl acetate in hexane) gave 4-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide (454 mg, 63%) as a brown oil. MS (ESI+) cald. for C17H15NO3S [(M+H)+] 313, obsd. 314.

後処理

  1. customwas degassed with argon
  2. temperaturecooled to room temperature
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-29c8b36c6f7d4c1f91e31f412ae7f1f8
出典データセット
uspto-grants-2012_02
特許番号
US08124629B2

関連ノート

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