Carbon Disulfide → 1-Benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine

HRID 977950ノート

反応式

HRID 977950 の反応式
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][C:11]1=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:18](=[S:20])=[S:19].Cl/[CH:22]=[CH:23]\Cl>CS(C)=O>[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[C:12](=[C:18]2[S:20][CH:23]=[CH:22][S:19]2)[C:11]1=[O:17])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 643833cis-1,2-DichloroethyleneHCID 224955411-Benzylpiperidine-2,4-dione

生成物 1

HCID 136065591-Benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒3 回

実験手順

Sodium hydride (60% despersion in oil) (432 mg) is suspended in dimethylsulfoxide (10 ml), and to the suspension is added dropwise a solution of 1-benzyl-2,4-dioxopiperidine (1.0 g) and carbon disulfide (0.33 ml) in dimethylsulfoxide (20 ml). The mixture is stirred for 2 hours, and thereto is added dropwise a solution of cis-1,2-dichloroethylene (0.42 ml) in dimethylsulfoxide (5 ml). The mixture is stirred at room temperature for 1.5 hour and further at 50° C. for 1 hour. The reaction mixture is poured onto water and extracted with benzene. The extract is washed with water, dried and then distilled to remove the solvent. The residue is recrystallized from isopropyl alcohol to give 1-benzyl-3-(1,3-dithiol-2-ylidene)-2,4- dioxopiperidine (486 mg) as pale yellow needles. m.p. 122°-124° C.

後処理

  1. stirringThe mixture is stirred at room temperature for 1.5 hour and further at 50° C. for 1 hour
  2. additionThe reaction mixture is poured onto water
  3. extractionextracted with benzene
  4. washThe extract is washed with water
  5. customdried
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue is recrystallized from isopropyl alcohol

出典と根拠

ORDレコード
ord-cb7aef7f2e6e4f0a93b9032debeec418
出典データセット
uspto-grants-1987_05
特許番号
US04663319

反応ノート

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