tert-Butylsulfinamide, (S)-(-)- → (NE,S)-N-[(4-chloro-3,5-dimethylphenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1629734ノート

反応式

HRID 1629734 の反応式
[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH3:11].[CH3:12][C:13]([S@@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5](/[CH:6]=[N:18]/[S@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])=[CH:4][C:3]=1[CH3:11]

参加物

5

反応物 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 222596964-Chloro-3,5-dimethylbenzaldehyde

生成物 1

HCID 58374474(NE,S)-N-[(4-chloro-3,5-dimethylphenyl)methylidene]-2-methylpropane-2-sulfinamide

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

A solution of 4-chloro-3,5-dimethyl-benzaldehyde (2 g, 11.86 mmol) and (S)-2-methylpropane-2-sulfinamide (1.58 g, 13.05 mmol) in toluene (35 mL) was treated with titanium(IV) isopropoxide (5.27 mL, 17.79 mmol). The mixture was stirred at 50° C. for 24 hours. It was then quenched with 10% sodium bicarbonate solution (50 mL) and extracted twice with EtOAc. The organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The crude was purified by chromatography on silica gel (cyclohexane/EtOAc).

後処理

  1. customIt was then quenched with 10% sodium bicarbonate solution (50 mL)
  2. extractionextracted twice with EtOAc
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by chromatography on silica gel (cyclohexane/EtOAc)

出典と根拠

ORDレコード
ord-df4e142fd0454214bc944c15e0f05826
出典データセット
uspto-grants-2014_07
特許番号
US08791100B2

反応ノート

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