Sodium Hydroxide → HCID 178464625, compound

Participants

Reaction Steps

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.

Provenance & Evidence