反应详情

A mixture of 8.80 g of a 50% aqueous sodium hydroxide solution, 13.44 g of methylguanidine sulfate and 100 ml acetone is stirred for 21/2 hrs at RT. 6.0 g of anhydrous sodium sulfate are added to the mixture, and stirring continued for 1 hr. 4-methoxyphenylacetyl chloride (9.23 g) in 50 ml acetone is added, and the reaction mixture stirred overnight at RT. The reaction mixuture is filtered and the filtrate is diluted with 100 ml of saturated aqueous sodium bicarbonate and the acetone evaporated in vacuo. The aqueous phase is diluted with 100 ml H2O and extracted with two 100 ml portions of methylene chloride. The combined organic extracts are dried with sodium sulfate, filtered and concentrated in vacuo. The resulting preccipitate is dissolved in a small volume of methanol and acidified with ethereal hydrochloric acid. The solvent is evaporated in vacuo, and the residue stirred with 200 ml of diethyl ether. The solid is collected, dried in air and recrystallized from acetonitrile to afford 4.80 g of white solid, M.P. 189° C.

1. stirringstirring
2. waitcontinued for 1 hr
3. stirringthe reaction mixture stirred overnight at RT
4. filtrationThe reaction mixuture is filtered
5. additionthe filtrate is diluted with 100 ml of saturated aqueous sodium bicarbonate
6. customthe acetone evaporated in vacuo
7. additionThe aqueous phase is diluted with 100 ml H2O
8. extractionextracted with two 100 ml portions of methylene chloride
9. dry with materialThe combined organic extracts are dried with sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. dissolutionThe resulting preccipitate is dissolved in a small volume of methanol
13. customThe solvent is evaporated in vacuo
14. stirringthe residue stirred with 200 ml of diethyl ether
15. customThe solid is collected
16. customdried in air
17. customrecrystallized from acetonitrile