Potassium Hydroxide → 1,5-diamino-3-(4-fluorophenyl)-1H-pyrazole

HRID 902202ノート

反応式

HRID 902202 の反応式
[NH2:1]OS(O)(=O)=O.[NH2:7][C:8]1[NH:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:9]=1.[OH-].[K+]>>[NH2:1][N:12]1[C:8]([NH2:7])=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:11]1

参加物

4

反応物 3

HCID 14797Potassium Hydroxide2 回HCID 76284hydroxylamine-O-sulfonic acid2 回HCID 178507289HCID 178507289、化合物

生成物 1

HCID 230848951,5-diamino-3-(4-fluorophenyl)-1H-pyrazole収率 14.9%

反応条件

温度
80 °C

実験手順

Hydroxylamine-O-sulfonic acid (2.26 g, 20.0 mmol) was portionwise added to aqueous solution (100 mL) containing 5-amino-3-(4-fluorophenyl)-1H-pyrazole (2.0 g, 11.3 mmol) and potassium hydroxide (2.52 g, 45 mmol) while stirring at 80° C. After the mixture was stirred at 80° C. for 30 minutes, potassium hydroxide (2.52 g, 45 mmol) was added thereto, hydroxylamine-O-sulfonic acid (2.26 g, 20.0 mmol) was portionwise added, and the mixture was stirred for further 1 hour. The reaction solution was cooled down to room temperature, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous potassium carbonate, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (C-300, hexane:ethyl acetate=1:2) to obtain the title compound (324 mg, 14.9%).

後処理

  1. stirringAfter the mixture was stirred at 80° C. for 30 minutes
  2. stirringthe mixture was stirred for further 1 hour
  3. temperatureThe reaction solution was cooled down to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (C-300, hexane:ethyl acetate=1:2)

出典と根拠

ORDレコード
ord-4131979826d2487cbb0c59bb833e4b86
出典データセット
uspto-grants-2008_04
特許番号
US07365079B2

反応ノート

読み込み中…