反应详情

8.80 g of a 50% aqueous sodium hydroxide solution, ethylguanidine sulfate (14.98 g), and 100 ml of acetone are stirred for 21/2 hrs at RT. The resulting mixture is treated with anhydrous sodium sulfate (6.0 g) and stirring continued for 1 hr. A solution of 3-methoxyphenylacetyl chloride (9.23 g) in 50 ml acetone is added to the mixture dropwise and the reaction mixture stirred overnight at RT. The mixture is filtered and the filtrate diluted with saturated aqueous sodium bicarbonate. The acetone is evaporated in vacuo. The aqueous residue is diluted with 100 ml of H2O and extracted with two 100 ml portions of methylene chloride. The combined extracts are dried with sodium sulfate, filtered and concentrated in vacuo. The resulting solution is acidified with ethereal hydrochloric acid and the solvent evaporated in vacuo. The residue is stirred with 200 ml of diethyl ether and the solid collected, washed with diethyl ether and recrystallized from acetone, affording the product, M.P. 108°-110° C.

1. stirringthe reaction mixture stirred overnight at RT
2. filtrationThe mixture is filtered
3. additionthe filtrate diluted with saturated aqueous sodium bicarbonate
4. customThe acetone is evaporated in vacuo
5. additionThe aqueous residue is diluted with 100 ml of H2O
6. extractionextracted with two 100 ml portions of methylene chloride
7. dry with materialThe combined extracts are dried with sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customthe solvent evaporated in vacuo
11. stirringThe residue is stirred with 200 ml of diethyl ether
12. customthe solid collected
13. washwashed with diethyl ether
14. customrecrystallized from acetone
15. customaffording the product, M.P. 108°-110° C.