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

HRID 977950노트

반응식

HRID 977950 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb7aef7f2e6e4f0a93b9032debeec418
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04663319

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