反应详情

8.80 g of a 50% aqueous sodium hydroxide solution, methylguanidine sulfate (13.44 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 4-chlorophenylacetylchloride (9.45 g) in 50 ml of acetone is added to the mixture dropwise, and stirring continued overnight at RT. The reaction mixture is filtered, the filtrate diluted with 100 ml of saturated sodium bicarbonate and the acetone evaporated in vacuo. The aqueous residue is diluted with 100 ml of H2O and extracted with three 100 ml portions of methylene chloride. The combined organic extract is dried with sodium sulfate, filtered and concentrated in vacuo. The resulting yellow solution is treated with ethereal hydrochloric acid and evaporated in vacuo. The residue is stirred with diethyl ether for 1/2 hr. The diethyl ether insoluble solid is collected and dried in air. The product is recrystallized from acetonitrile to afford 5.66 g of a white crystalline solid, M.P. 183°-184° C.

1. stirringstirring continued overnight at RT
2. filtrationThe reaction mixture is filtered
3. additionthe filtrate diluted with 100 ml of saturated sodium bicarbonate
4. customthe acetone evaporated in vacuo
5. additionThe aqueous residue is diluted with 100 ml of H2O
6. extractionextracted with three 100 ml portions of methylene chloride
7. extractionThe combined organic extract
8. dry with materialis dried with sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. additionThe resulting yellow solution is treated with ethereal hydrochloric acid
12. customevaporated in vacuo
13. stirringThe residue is stirred with diethyl ether for 1/2 hr
14. customThe diethyl ether insoluble solid is collected
15. customdried in air
16. customThe product is recrystallized from acetonitrile