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Sodium Hydroxide → 4-(1H-1,2,4-triazol-1-yl)benzamide

HRID 587827
ノート
印刷プレビュー

反応式

HRID 587827 の反応式
BrC1C=C(C(F)(C(F)(F)F)C(F)(F)F)C=C(Br)C=1[NH2:4].[N:20]1([C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=2)[CH:24]=[N:23][CH:22]=[N:21]1.[OH-].[Na+]>N1C=CC=CC=1.O.O1CCCC1>[N:20]1([C:25]2[CH:33]=[CH:32][C:28]([C:29]([NH2:4])=[O:30])=[CH:27][CH:26]=2)[CH:24]=[N:23][CH:22]=[N:21]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 103198952,6-Dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)anilineHCID 450819094-(1H-1,2,4-Triazol-1-yl)benzoyl chloride

生成物 1

HCID 219505584-(1H-1,2,4-triazol-1-yl)benzamide収率 89%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回
HCID 1049
Pyridine
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

2,6-Dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)aniline (0.45 g) was dissolved in pyridine (5 ml). To the solution, the crude product of 4-(1H-1,2,4-triazol-1-yl)benzoyl chloride (0.45 g) was added and the mixture was refluxed under heating for 1.5 hours. After cooling to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with 2N hydrochloric acid and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a residue, which were then dissolved in tetrahydrofuran (20 ml), added with a 2N sodium hydroxide solution (5 ml) and stirred under heating at 50° C. for 2 hours. After cooling to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with water and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain N-[2,6-d]bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-(1H-1,2,4-triazol-1-yl)benzamide (0.18 g, yield 28%).

後処理

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1.5 hours
  3. extractionextracted twice with ethyl acetate
  4. washwashed with 2N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtering off the drying agent
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain a residue, which
  9. temperatureunder heating at 50° C. for 2 hours
  10. temperatureAfter cooling to room temperature
  11. extractionextracted twice with ethyl acetate
  12. washwashed with water
  13. dry with materialdried over magnesium sulfate
  14. filtrationAfter filtering off the drying agent
  15. distillationthe solvent was distilled off under reduced pressure
  16. customto obtain a crude product
  17. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-551b944f0d004f0598bb772b655bf9aa
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09227923B2

反応ノート

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