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Potassium Carbonate → 1-[4-chloro-2-fluoro-5-(5-hydroxypyridin-2-yloxy)-phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl,1,2,4-triazol-5(1H)-one

HRID 1090985
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HRID 1090985 반응식
C(=O)([O-])[O-:2].[K+].[K+].F[B-](F)(F)F.[Cl:12][C:13]1[CH:27]=[C:26]([F:28])[C:25]([N:29]2[C:33](=[O:34])[N:32]([CH:35]([F:37])[F:36])[C:31]([CH3:38])=[N:30]2)=[CH:24][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([N+]#N)=[CH:18][N:17]=1>FC(F)(F)C(O)=O.O>[Cl:12][C:13]1[C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:2])=[CH:18][N:17]=2)=[CH:24][C:25]([N:29]2[C:33](=[O:34])[N:32]([CH:35]([F:36])[F:37])[C:31]([CH3:38])=[N:30]2)=[C:26]([F:28])[CH:27]=1
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참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 199122182-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]pyridine-5-diazonium tetrafluoroborate

생성물 1

HCID 199122291-[4-chloro-2-fluoro-5-(5-hydroxypyridin-2-yloxy)-phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl,1,2,4-triazol-5(1H)-one수율 177.8%

시약·촉매·용매 2

HCID 962Water용매
HCID 6422
Trifluoroacetic acid
용매

실험 절차

To a stirred, cold (ice bath) solution of 0.67 g (0.0048 mole) of potassium carbonate in 20 mL of trifluoroacetic acid was added 4.7 g (0.097 mole) of 2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro -3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]pyridine-5-diazonium tetrafluoroborate. The reaction mixture was allowed to warm to room temperature and was then heated at reflux for 5.5 hours. The mixture was cooled to room temperature, diluted with 50 mL of water, and the whole was extracted with four portions of methylene chloride. The extracts were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to give a red oil which was purified by column chromatography on silica gel. Elution with n-hexane:ethyl acetate (2:1) gave 3.3 g of 1-[4-chloro-2-fluoro-5-(5-hydroxypyridin-2-yloxy)-phenyl]-4-difluoromethyl-4,5-dihydro -3-methyl,1,2,4-triazol-5(1H)-one as a solid, m.p. 179°-181° C.

후처리

  1. temperaturewas then heated
  2. temperatureat reflux for 5.5 hours
  3. temperatureThe mixture was cooled to room temperature
  4. extractionthe whole was extracted with four portions of methylene chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customto give a red oil which
  9. customwas purified by column chromatography on silica gel
  10. washElution with n-hexane:ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-2c5007295b1e417581b0f6b16953c6ce
출처 데이터셋
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05084085

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