Hydroxide → 2-(1-Imidazolyl)-2-{4-(hydroxyphenyl)-1,3-dithiolane-2-ylidene}acetonitrile

HRID 274856노트

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HRID 274856 반응식
[C:1]([CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)#[N:2].[C:9](=[S:11])=[S:10].[OH-].S1C=CC(C([O-])=[O:19])S1.Br[CH:22]([C:25]1[CH:30]=[CH:29][C:28](OC(C)(C)C)=[CH:27][CH:26]=1)[CH2:23]Br>CS(C)=O>[N:4]1([C:3](=[C:9]2[S:11][CH:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[OH:19])[CH2:23][S:10]2)[C:1]#[N:2])[CH:8]=[CH:7][N:6]=[CH:5]1

참가 물질

7

반응물 5

HCID 961HydroxideHCID 6348Carbon DisulfideHCID 11804695(1-Imidazolyl)acetonitrileHCID 152334951,2-Dibromo-1-(4-t-butoxyphenyl)ethaneHCID 86638310Dithiolate

생성물 1

HCID 537947732-(1-Imidazolyl)-2-{4-(hydroxyphenyl)-1,3-dithiolane-2-ylidene}acetonitrile수율 16.8%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

In 40 ml of dimethyl sulfoxide were dissolved 4.6 g (0.004 mol) of 1-cyanomethylimidazole, 3.1 g (0.005 mol) of carbon disulfide and 5.2 g of pottassium hydroxide powder by stirring at room temperature for 1 hour to prepare a dithiolate solution. The solution was added dropwise to a solution of 14.8 g (0.04 mol) of 1,2-dibromo-1-(4-t-butoxyphenyl)ethane in 40 ml of dimethyl sulfoxide at 30° C., followed by stirring for 2 hours. To the reaction mixture was added 200 ml of icewater, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to obtain a mixture of geometric isomers as a viscous oily substance. Purification of the product by silica gel chromatography gave 2.4 g (yield: 16.8%) of a Z-isomer and 4.5 g (yield: 31.5%) of an E-isomer both as a viscous oily substance.

후처리

  1. stirringby stirring for 2 hours
  2. additionTo the reaction mixture was added 200 ml of icewater
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto obtain
  8. additiona mixture of geometric isomers as a viscous oily substance
  9. customPurification of the product by silica gel chromatography
  10. customgave 2.4 g (yield: 16.8%) of a Z-isomer and 4.5 g (yield: 31.5%) of an E-isomer

출처 및 근거

ORD 기록
ord-e9318161b6864b47bc285047657ab466
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391558

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