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Sodium hydride → 1-Ethyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine

HRID 977940
ノート
印刷プレビュー

反応式

HRID 977940 の反応式
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][C:4]1=[O:10])[CH3:2].[H-].[Na+].[I-].CS[C:16]1[S:20][CH:19]=[CH:18][S+:17]=1>CN(C)C=O>[CH2:1]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[C:5](=[C:16]2[S:20][CH:19]=[CH:18][S:17]2)[C:4]1=[O:10])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 137841191-Ethylpiperidine-2,4-dioneHCID 19751531(2H-1,3-Dithiol-2-ylidene)(methyl)sulfanium iodide

生成物 1

HCID 136065471-Ethyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine収率 66.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

1-Ethyl-2,4-dioxopiperidine (1.06 g) is dissolved in N,N-dimethylformamide (50 ml), and the solution is added dropwise to a suspension of sodium hydride (60% dispersion in oil, 332 mg) in N,N-dimethylformamide (50 ml) under ice-cooling. The mixture is stirred for 20 minutes, and thereto is added 2-methylthio-1,3-dithiolium iodide (1.89 g). After stirring at room temperature overnight, the reaction mixture is poured onto water and extracted with ethyl acetate. The extract is washed with water, dried and distilled to remove the solvent. The residue is purified by silica gel column chromatography (developer: ethyl acetate) and then recrystallized from ethyl acetate-isopropyl ether to give 1-ethyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine (1.10 g) as pale yellow needles. m.p. 114.5°-117° C.

後処理

  1. temperaturecooling
  2. stirringAfter stirring at room temperature overnight
  3. additionthe reaction mixture is poured onto water
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography (developer: ethyl acetate)
  10. customrecrystallized from ethyl acetate-isopropyl ether

出典と根拠

ORDレコード
ord-de4c72ee6b95497b9fdc796c9f679983
出典データセット
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04663319

反応ノート

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