反応 #318027

反応方程式

water

sodium hydride

Intermediate 18

3-Amino-N-hydroxybenzenecarboximidamide

methyl acetate

→

title compound

3-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度the mixture heated
3. 3
   温度under reflux for 16 h
4. 4
   温度After cooling to 20° C. the mixture
5. 5
   抽出extracted with ethyl acetate
6. 6
   洗浄The combined organic layers were washed with brine
7. 7
   乾燥dried over magnesium sulphate
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The residue was purified by chromatography on silica gel
10. 10
    洗浄eluting with dichloromethane

実験手順

To a stirred solution of Intermediate 18 (5.3 g) in dry tetrahydrofuran (50 ml) was added 4 Å molecular sieves, followed by sodium hydride (60% dispersion in mineral oil; 1.5 g) and the mixture heated at 65° C. for 30 min. After cooling to room temperature methyl acetate (2.8 ml) was added and the mixture heated under reflux for 16 h. After cooling to 20° C. the mixture was added to water (100 ml) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with dichloromethane to give the title compound as a white solid (4.0 g).

出典