Cyanogen Bromide → 5-[(4-Fluorophenyl)methyl]-1,3,4-oxadiazol-2-amine

HRID 1822892ノート

反応式

HRID 1822892 の反応式
Br[C:2]#[N:3].[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:14][NH2:15])=[O:13])=[CH:7][CH:6]=1>CO>[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[O:13][C:2]([NH2:3])=[N:15][N:14]=2)=[CH:7][CH:6]=1

参加物

4

反応物 2

HCID 10476Cyanogen BromideHCID 37716122-(4-Fluorophenyl)acetohydrazide

生成物 1

HCID 219193195-[(4-Fluorophenyl)methyl]-1,3,4-oxadiazol-2-amine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
2.5 °C

実験手順

Solid BrCN 13.37 g (130 mmol, 1.1 eq.) was added in one portion into ice-cooled slurry of (4-Fluoro-phenyl)-acetic acid hydrazide (19.85 g, 118 mmol) and KHCO3 14.77 g (147.5 mmol, 1.25 eq.) in MeOH (150 mL) in a 1L flask. (Followed by MeOH 10 mL to wash the funnel). The mixture was stirred on ice bath at 0-5° C. for 2 hours in a loose-capped flask, then the bath allowed to melt gradually and then the mixture was stirred at 5 to 20° C. overnight (17 hrs). The reaction mixture was diluted with water (200 mL), stirred for 1 hour in an open flask, then cooled on ice bath. The precipitate was collected by filtration, washed with water and dried on highvac. [1st fraction]The supernatants were concentrated on rotavap form warm (40° C.) water bath to remove all MeOH and some water. The obtained slurry was cooled to room temperature, the precipitate was collected by filtration, washed with water and dried on highvac. [2nd fraction]. Combined yield: 20.836 g (91.5%) of a white crystalline solid.

後処理

  1. washto wash the funnel)
  2. stirringthe mixture was stirred at 5 to 20° C. overnight (17 hrs)
  3. additionThe reaction mixture was diluted with water (200 mL)
  4. stirringstirred for 1 hour in an open flask
  5. temperaturecooled on ice bath
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customdried on highvac
  9. concentration[1st fraction]The supernatants were concentrated on rotavap form
  10. temperaturewarm (40° C.) water bath
  11. customto remove all MeOH
  12. temperatureThe obtained slurry was cooled to room temperature
  13. filtrationthe precipitate was collected by filtration
  14. washwashed with water
  15. customdried on highvac

出典と根拠

ORDレコード
ord-090a6af3306d4c7c9c294f3515cdf504
出典データセット
uspto-grants-2006_05
特許番号
US07037909B2

反応ノート

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