Thiophosgene → HCID 19005818, compound

Participants

Reaction Steps

Thiophosgene (0.12 mL, 1.56 mmol) is added to a solution of the above prepared formula III 6-amino-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid (170 mg, 0.521 mmol) and methanol (25 mL). The reaction mixture is stirred for five minutes at room temperature and then concentrated in vacuo. The residue is redissolved into a small amount of methanol, filtered and the filtrate is added to 25 mL of ether. The resulting precipitate is collected, washed with ether and dried under reduced pressure to give 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) -6-isothiocyano-3-quinolinecarboxylic acid as a brown powder (190 mg). The product is obtained in the form of a tricyclic anhydride which hydrolyses to the acid in water or during subsequent reaction in aqueous media. The purity of this material is determined by TLC on silica gel with chloroform, methanol and acetic acid (220:30:6) elution.

Provenance & Evidence