Acetone → HCID 20430573, compound

Participants

Reaction Steps

A suspension of 8.00 g of 50% aqueous NaOH, 19.92 g of 2-pyridylmethyl guanidine sulfate and 100 ml of acetone is stirred for 31/2 hrs. at RT. 8 g of anhydrous sodium sulfate is added to the suspension and the reaction mixture stirred for 2 hrs. The reaction mixture is treated dropwise with a solution of 4.35 ml propionyl chloride in 100 ml acetone, stirred overnight at RT and filtered. The filtrate is evaporated in vacuo to a tan oil. The oil is dissolved in 100 ml of methylene chloride and the resulting solution is washed with H2O. The aqueous layer is extracted with methylene chloride. The combined organic extract is dried over sodium sulfate, filtered and evaporated in vacuo (0.1 mm) to an oil. The residue is dissolved in hot 2-propanol, 3.32 g succinic acid added, and the resulting mixture heated until a solid begins to form. The solid is collected, washed with 2-propanol and dried in vacuo to yield the desired guanidine succinate as a white powder, M.P. 168°-170° C.

Provenance & Evidence