Dicyclohexylcarbodiimide → 6-Amidino-1-(2-carbamoylvinyl)-2-naphthyl 4-aminoiminomethylaminobenzoate.dihydrochloride

Participants

Reaction Steps

90 Milliliters of 20% hydrous pyridine was added to 5.08 g of 4-aminoiminomethylaminobenzoic acid.methanesulfonate, 4.5 g of 6-amidino-1-(2-carbamoylvinyl)-2-naphthol.hydrochloride, 6.34 g of DCC and 80 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 48 hours at room temperature. Then, the precipitate was collected by filtration and washed twice with 160 ml of warm 20% hydrous pyridine. The above-obtained reaction filtrate and the warm hydrous pyridine wash liquid were combined and the resulting solution was added to 1 liter of acetone, followed by stirring for 24 hours under cooling with ice. The precipitate was collected by filtration and thereto was added 70 ml of warm DMF to dissolve the precipitate. Then, 0.5 g of active carbon was added, followed by stirring for 30 minutes at room temperature. Insoluble matter was filtered and 8.4 ml of concentrated hydrochloric acid was added to the filtrate. The resulting solution was added dropwise to 600 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 6.8 g of the desired product.

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