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

HRID 977947ノート

反応式

HRID 977947 の反応式
[H-].[Na+].[S:3]1[CH:7]=[CH:6][S:5][C:4]1=[C:8]1[C:13](=[O:14])[CH2:12][CH2:11][NH:10][C:9]1=[O:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([N:10]1[CH2:11][CH2:12][C:13](=[O:14])[C:8](=[C:4]2[S:5][CH:6]=[CH:7][S:3]2)[C:9]1=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 136065623-(1,3-Dithiol-2-ylidene)-2,4-dioxopiperidine

生成物 1

HCID 136065591-Benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine収率 62%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Sodium hydride (60% dispersion in oil) (47 mg) is suspended in N,N-dimethylformamide (2 ml), and to the suspension is added dropwise a solution of 3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine (200 mg) in N,N-dimethylformamide (16 ml). The mixture is stirred for 10 minutes and thereto is added benzyl bromide (0.12 ml), and the mixture is further stirred for 1 hour. After the reaction, the reaction mixture is distilled to remove the solvent under reduced pressure and the residue is dissolved in chloroform. The chloroform solution is washed with an aqueous saturated sodium chloride solution, 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 (176 mg, 62%) as pale yellow needles. m.p. 122°-124° C.

後処理

  1. stirringthe mixture is further stirred for 1 hour
  2. customAfter the reaction
  3. distillationthe reaction mixture is distilled
  4. customto remove the solvent under reduced pressure
  5. dissolutionthe residue is dissolved in chloroform
  6. washThe chloroform solution is washed with an aqueous saturated sodium chloride solution
  7. customdried
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe residue is recrystallized from isopropyl alcohol

出典と根拠

ORDレコード
ord-6b1b8a3f5a2f4561ab3fb83a0b95aabd
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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