Water → HCID 20311737, compound

Participants

Reaction Steps

Six grams of 1-(1-naphthyl)-1-methylamino-2-aminoethane, dihydrochloride, prepared in Part A, are stirred into 25 ml of water. Thereafter 35 ml of saturated sodium bicarbonate are added and stirred for several minutes. Then 160 ml of isopropanol followed by 4.16 g of 1,3-bis(methoxycarbonyl)-S-methylisothiourea dissolved in 120 ml of chloroform are added to the mixture. The resulting mixture is stirred under nitrogen for 7 days. The organic solvents are removed in a rotary evaporator and 10% aqueous HCl is added until the pH of the mixture is just acidic. The resulting mixture is extracted with ether and the aqueous mixture is neutralized with saturated sodium bicarbonate, filtered, and pumped dry to give 5.3 g of crude 1-methyl-4,5-dihydro-2-(methoxycarbonylamino)-5-(1-naphthyl)-imidazole, m.p. 187°-190° C. One gram of the crude material is recrystallized from ethanol to give 0.77 g of more pure material, m.p. 194°-197° C.

Provenance & Evidence