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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
ノート
印刷プレビュー

反応式

HRID 1090985 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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)-one収率 177.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6422
Trifluoroacetic acid
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2c5007295b1e417581b0f6b16953c6ce
出典データセット
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05084085

反応ノート

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