Sodium hydride → 3-Bromo-5-(1,1-dioxo-isothiazolidin-2-ylmethyl)-pyridine

HRID 391320

反応式

HRID 391320 の反応式
[O:1]=[S:2]1(=[O:7])[CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].Cl.[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18]Cl)[CH:17]=1>CN(C=O)C>[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18][N:3]2[CH2:4][CH2:5][CH2:6][S:2]2(=[O:7])=[O:1])[CH:17]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 6421571,3-PropanesultamHCID 125150693-Bromo-5-(chloromethyl)pyridine hydrochloride

生成物 1

HCID 595783953-Bromo-5-(1,1-dioxo-isothiazolidin-2-ylmethyl)-pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A 40 mL scintillation vial was charged with 1,1-dioxo-isothiazolidine (115 mg, 0.949 mmol) and DMF (3 mL). The reaction mixture was cooled to 0° C. and sodium hydride (95 mg, 2.373 mmol) was added. The reaction was left to stir at room temperature for 20 min followed by the addition of 3-bromo-5-(chloromethyl)pyridine hydrochloride (277 mg, 1.139 mmol). The reaction was stirred at room temperature for 3 h, then quenched with water and extracted with ethyl acetate. The organic layer was washed with water twice, dried over sodium sulfate and concentrated in vacuo. The crude was purified by silica gel flash chromatography using heptane-ethyl acetate (60-40, v/v) to afford 3-bromo-5-(1,1-dioxo-isothiazolidin-2-ylmethyl)-pyridine as a colorless oil. MS (ESI) m/z 292.9 (M+H)+

後処理

  1. waitThe reaction was left
  2. stirringThe reaction was stirred at room temperature for 3 h
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water twice
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-a91e67409bb14e688411671e529901f9
出典データセット
uspto-grants-2013_02
特許番号
US08383827B2

関連ノート

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