反应详情

A mixture of 8.80 g of an aqueous sodium hydroxide solution (50%), ethylguanidine sulfate (14.98 g), and 100 ml of acetone, are stirred for 21/2 hrs at RT. The resulting mixture is then treated with anhydrous sodium sulfate (6.0 g) and stirring is continued for 1 hr. A solution of 5-methyl-3-phenyl-4-isoxazoloyl chloride (11.08 g) in 50 ml acetone is added dropwise and the resulting mixture is stirred overnight at RT. The reaction mixture is filtered, the filtrate diluted with 100 ml of saturated aqueous sodium bicarbonate and the acetone evaporated in vacuo. The aqueous residue is diluted with 100 ml H2O and extracted with two 100 ml portions of methylene chloride. The combined organic extract is dried, filtered and concentrated in vacuo. The residue is acidified with ethereal hydrochloric acid and evaporated in vacuo. The residue is stirred with 200 ml of diethyl ether, the solid collected and washed with diethyl ether. Recrystallization from acetonitrile affords 11.7 g of white crystalline product, M.P. 215° C.

1. stirringstirring
2. waitis continued for 1 hr
3. stirringthe resulting mixture is stirred overnight at RT
4. filtrationThe reaction mixture is filtered
5. additionthe filtrate diluted with 100 ml of saturated aqueous sodium bicarbonate
6. customthe acetone evaporated in vacuo
7. additionThe aqueous residue is diluted with 100 ml H2O
8. extractionextracted with two 100 ml portions of methylene chloride
9. extractionThe combined organic extract
10. customis dried
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customevaporated in vacuo
14. stirringThe residue is stirred with 200 ml of diethyl ether
15. customthe solid collected
16. washwashed with diethyl ether
17. customRecrystallization from acetonitrile