Carbon Disulfide → ethyl 2-(1,3-dithiol-2-ylidene)-2-(N-benzylcarbamoyl)acetate

HRID 977952노트

반응식

HRID 977952 반응식
[CH2:1]([NH:8][C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](=[S:19])=[S:18].[OH-].[K+].Cl/[CH:23]=[CH:24]\Cl>CS(C)=O.O>[S:18]1[CH:24]=[CH:23][S:19][C:17]1=[C:11]([C:9](=[O:10])[NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

7

반응물 4

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 643833cis-1,2-Dichloroethylene2회HCID 11379032Ethyl 3-(benzylamino)-3-oxopropanoate

생성물 1

HCID 20204019ethyl 2-(1,3-dithiol-2-ylidene)-2-(N-benzylcarbamoyl)acetate수율 62.8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회

실험 절차

Ethyl (N-benzylcarbamoyl)acetate (39.00 g) and carbon disulfide (14.03 g) are dissolved in dimethylsulfoxide (390 ml). A solution of potassium hydroxide (21.52 g) in water (39 ml) is added dropwise to the mixture at 20° to 40° C. The mixture is stirred at the same temperature for 30 minutes, and then cis-1,2-dichloroethylene (17.84 g) is added dropwise thereto. The mixture is stirred at 50° C. for 5 hours. Cis-1,2-dichloroethylene (3.24 g) is further added to the mixture 3 hours after the commencement of the reaction. After cooling, the mixture is poured into 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 purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate=2:1), and then recrystallized from a mixture of n-hexane and ethyl acetate, whereby ethyl 2-(1,3-dithiol-2-ylidene)-2-(N-benzylcarbamoyl)acetate (33.77 g) is obtained as pale yellow prisms. Yield: 62.8%.

후처리

  1. stirringThe mixture is stirred at 50° C. for 5 hours
  2. customafter the commencement of the reaction
  3. temperatureAfter cooling
  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 purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate=2:1)
  10. customrecrystallized from a mixture of n-hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-cd08dec0f9c14a658a70021c9cba4417
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04663319

반응 노트

불러오는 중…