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Acetonitrile → HCID 21298702, 화합물

HRID 364320
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HRID 364320 반응식
[F:1][C:2]([F:10])([CH:7]([F:9])[F:8])[CH2:3][N:4]=[C:5]=S.C1(=O)[N:15]([CH2:16][CH2:17][CH2:18][S:19][C:20]2[N:25]=[C:24]([NH2:26])[CH:23]=[CH:22][N:21]=2)C(=O)C2=CC=CC=C12.C(#[N:35])C>CN(C)C=O.N>[F:1][C:2]([F:10])([CH:7]([F:9])[F:8])[CH2:3][N:4]=[C:5]([NH2:35])[NH:26][C:24]1[CH:23]=[CH:22][N:21]=[C:20]([S:19][CH2:18][CH2:17][CH2:16][NH2:15])[N:25]=1
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참가 물질

6

반응물 3

HCID 6342AcetonitrileHCID 212797361,1,2,2-Tetrafluoro-3-isothiocyanatopropaneHCID 21298869HCID 21298869, 화합물

생성물 1

HCID 21298702HCID 21298702, 화합물

시약·촉매·용매 2

HCID 222Ammonia용매HCID 6228Dimethylformamide용매

실험 절차

2,2,3,3-Tetrafluoropropylisothiocyanate (0.9 g.) and 2-(3-phthalimidopropylthio)-4-aminopyrimidine (0.9 g.) were dissolved in acetonitrile (30 ml.) and heated under reflux for 64 hours. The resulting suspension was cooled, filtered and the collected solid washed with acetonitrile (10 ml.) to give a white solid (0.9 g.). This was dissolved in a mixture of dimethylformamide (10 ml.) and saturated ethanolic ammonia solution (5 ml.) and treated with yellow mercuric oxide (0.8 g.). The mixture was stirred at room temperature for 3 hours. The solvent was evaporated and the black residue was triturated with ethyl acetate and filtered. The solvent was evaporated and the residual gum was dissolved in ethanol (15 ml.) and added to a solution of hydrazine (5 ml.) in ethanol (10 ml.). The mixture was stirred at room temperature for 2 hours then the solvent was evaporated. The residue was triturated with 1N hydrochloric acid, filtered and the filtrate was basified with 10N sodium hydroxide solution. The product was extracted with ethyl acetate, dried (magnesium sulphate) and the solvent was evaporated to give 4-[2-(2,2,3,3-tetrafluoropropyl)guanidino]-2-[3-aminopropylthio]pyrimidine (0.5 g.) which was used without further purification.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 64 hours
  3. temperatureThe resulting suspension was cooled
  4. filtrationfiltered
  5. washthe collected solid washed with acetonitrile (10 ml.)
  6. customto give a white solid (0.9 g.)
  7. customThe solvent was evaporated
  8. customthe black residue was triturated with ethyl acetate
  9. filtrationfiltered
  10. customThe solvent was evaporated
  11. dissolutionthe residual gum was dissolved in ethanol (15 ml.)
  12. additionadded to a solution of hydrazine (5 ml.) in ethanol (10 ml.)
  13. stirringThe mixture was stirred at room temperature for 2 hours
  14. customthe solvent was evaporated
  15. customThe residue was triturated with 1N hydrochloric acid
  16. filtrationfiltered
  17. extractionThe product was extracted with ethyl acetate
  18. dry with materialdried (magnesium sulphate)
  19. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-e898f1fb6b5642c5bf8126cbfb326ea3
출처 데이터셋
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04604465

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