Hydrogen Sulfide → Methyl p-[2-(p-amidinobenzamido)ethyl]phenoxyacetate

Participants

Reaction Steps

H2S was passed for 45 minutes through a suspension of 2.0 g of methyl 4-[2-(p-cyanobenzamido)ethyl]phenoxyacetate in 24 ml of pyridine/triethylamine (7:1) at 0° C. The solution resulting after 12 hours was concentrated, and a suspension was made of the residue in methanol and filtered. The residue on the filter was immediately suspended in 30 ml of acetone, and 4 ml of methyl iodide were added. After 2.5 hours the precipitate was filtered off, washed with a little acetone and, after drying, dissolved in 20 ml of methanol. 2.0 g of ammonium acetate were added and the mixture was then left to react at room temperature for 2 hours, during which a colorless precipitate formed, and this was filtered off and reprecipitated from methanol. Methyl p-[2-(p-amidinobenzamido)ethyl]phenoxyacetate was obtained as the acetate salt, melting point above 200° C., after drying under high vacuum.

Provenance & Evidence