Phosgene → HCID 23169337, compound

Participants

Reaction Steps

To a solution of phosgene in toluene (1.5 ml, 1.9M) stirred under N2 at 0° C. was added dropwise 5-(2-aminophenyl)-3-cyclopropyl-1,2,4-oxadiazol (0.5 g, 2.5 mmol) in 30 mldry methylene chloride and then 0.8 ml of dry triethylamine. Upon addition the mixture was stirred at 0° C. for 15 min. whereupon a solution of 3-aminoquinuclidine (0.18 g, 1.4 mmol) in 10 ml CH2Cl2 was added. This mixture was stirred at room temperature for 4 h and washed with 25 ml saturated sodium bicarbonate. The organic phase was dried with magnesium sulphate and concentrated in vacuo. The resulting oil dissolved in methanol. Addition of ether precipitated 0.38 g of the desired product as white crystals. This product was dissolved in ethanol and precipitated as the hydrochloride by addition of dry hydrochloric acid in ether, giving0.3 g. M.p. 229°-233° C.

Provenance & Evidence