N,N,N',N'-Tetramethylmethanediamine → 4,5-Dihydro-4-(3-Methyl-5-Isoxazolyl)-3-Phenyl-N-(4-Trifluoromethoxyphenyl)-1H-Pyrazole-1-Carboxamide

HRID 36948

반응식

HRID 36948 반응식
CC1C=C(CC(C2C=CC=CC=2)=O)ON=1.CN(CN(C)C)C.FC(F)(F)C(O)=O.NN.[CH3:32][C:33]1[CH:37]=[C:36]([CH:38]2[CH2:42][NH:41][N:40]=[C:39]2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:35][N:34]=1.[F:49][C:50]([F:62])([F:61])[O:51][C:52]1[CH:57]=[CH:56][C:55]([N:58]=[C:59]=[O:60])=[CH:54][CH:53]=1>ClCCl.C(O)(=O)C>[CH3:32][C:33]1[CH:37]=[C:36]([CH:38]2[CH2:42][N:41]([C:59]([NH:58][C:55]3[CH:56]=[CH:57][C:52]([O:51][C:50]([F:49])([F:61])[F:62])=[CH:53][CH:54]=3)=[O:60])[N:40]=[C:39]2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:35][N:34]=1

참가 물질

9

반응물 6

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 109545992-(3-Methyl-5-isoxazolyl)-1-phenyl-1-ethanoneHCID 152392334,5-dihydro-4-(3-methyl-5-isoxazolyl)-3-phenyl-1H-pyrazole

생성물 1

HCID 152392344,5-Dihydro-4-(3-Methyl-5-Isoxazolyl)-3-Phenyl-N-(4-Trifluoromethoxyphenyl)-1H-Pyrazole-1-Carboxamide

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매2회

반응 조건

온도
-15 °C

실험 절차

A mixture of 20 mL of dichloromethane, 2.01 g (10 mmol) of 2-(3-methyl-5-isoxazolyl)-1-phenylethanone and 1.12 g (11 mmol) of N,N,N',N',-tetramethyldiaminomethane was prepared and cooled to -15° C. and 1.25 g (11 mmol) of trifluoroacetic acid in 5 mL of dichloromethane was added with cooling and stirring. Stirring was continued for 5 min at about 0° C. and then the mixture was allowed to warm to ambient temperature and stir for another 1.75 hr. A proton NMR spectrum of the mixture was taken which indicated complete disappearance of the starting material. Anhydrous hydrazine (0.96 g, 30 mmol) was added and the mixture was allowed to react with stirring for 2 hr. A proton NMR spectrum of the mixture indicated complete conversion to 4,5-dihydro-4-(3-methyl-5-isoxazolyl)-3-phenyl-1H-pyrazole. The mixture was washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, and filtered. 4-(Trifluoromethoxy)phenyl isocyanate (2.19 g, 10.8 mmol) was then added with stirring. The mixture was allowed to react for 1 hr and then 1 mL of acetic acid was added and the mixture was allowed to react for 5 min. It was then washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated by evaporation under reduced pressure. The resulting solid was extracted with boiling ether and air dried to obtain 3.1 g (72 percent of theory) of the title compound as a white solid melting at 195°-197° C.

후처리

  1. customwas prepared
  2. temperaturewith cooling
  3. stirringStirring
  4. temperatureto warm to ambient temperature
  5. stirringstir for another 1.75 hr
  6. customto react
  7. stirringwith stirring for 2 hr
  8. washThe mixture was washed with saturated aqueous sodium bicarbonate solution
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. stirringwith stirring
  12. customto react for 1 hr
  13. customto react for 5 min
  14. washIt was then washed with saturated aqueous sodium bicarbonate
  15. dry with materialdried over sodium sulfate
  16. filtrationfiltered
  17. concentrationconcentrated by evaporation under reduced pressure
  18. extractionThe resulting solid was extracted with boiling ether and air
  19. customdried

출처 및 근거

ORD 기록
ord-2be3dfa20ff140bd87f986b307c15730
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418247

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