Ethyl Acrylate → Ethyl 1-benzyl-5-(1,3-dithiol-2-ylidene)-4,6-dioxopiperidine-3-carboxylate

HRID 977953노트

반응식

HRID 977953 반응식
[H-].[Na+].[S:3]1[CH:7]=[CH:6][S:5][C:4]1=[C:8]([C:14](=[O:23])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]([O:11]CC)=O.[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH:25]=[CH2:26]>CN(C)C=O>[CH2:16]([N:15]1[C:14](=[O:23])[C:8](=[C:4]2[S:3][CH:7]=[CH:6][S:5]2)[C:9](=[O:11])[CH:25]([C:24]([O:28][CH2:29][CH3:30])=[O:27])[CH2:26]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

5

반응물 3

HCID 8821Ethyl AcrylateHCID 24758Sodium hydrideHCID 20204019ethyl 2-(1,3-dithiol-2-ylidene)-2-(N-benzylcarbamoyl)acetate

생성물 1

HCID 13934862Ethyl 1-benzyl-5-(1,3-dithiol-2-ylidene)-4,6-dioxopiperidine-3-carboxylate수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

Sodium hydride (a 60% dispersion in oil) (1.50 g) is suspended in N,N-dimethylformamide (100 ml) and a solution of ethyl 2-(1,3-dithiol-2-ylidene)-2-(N-benzylcarbamoyl)acetate (10.0 g) in dimethylformamide (250 ml) is added dropwise thereto at 4° to 5° C. The mixture is stirred at the same temperature for 30 minutes. A solution of ethyl acrylate (4.1 ml) in dimethylformamide (100 ml) is added dropwise to the mixture, and the mixture is stirred at the same temperature for one hour and then at room temperature for 5 hours. The mixture is poured into ice-water, and the aqueous solution is extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove the solvent. The residue is recrystallized from a mixture of n-hexane and ethyl acetate, whereby ethyl 1-benzyl-5-(1,3-dithiol-2-ylidene)-4,6-dioxopiperidine-3-carboxylate (8.76 g ) is obtained as pale yellow needles. Yield: 75%.

후처리

  1. customat 4° to 5° C
  2. stirringthe mixture is stirred at the same temperature for one hour
  3. waitat room temperature for 5 hours
  4. extractionthe aqueous solution is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. customevaporated
  8. customto remove the solvent
  9. customThe residue is recrystallized from a mixture of n-hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-80759b6916004bb7bbee9c74aca4efa6
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04663319

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