Methyl isothiocyanate → 1-{2-[(N-methylthiocarbamoyl)amino]ethyl}-5,7-dimethyl-1,8-naphthyridin-2(1H)-one
Reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[C:9]([CH3:15])[CH:10]=[C:11]([CH3:14])[N:12]=2)[CH:7]=[CH:6][C:5]1=[O:16].[CH3:17][N:18]=[C:19]=[S:20]>O>[CH3:17][NH:18][C:19]([NH:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[C:9]([CH3:15])[CH:10]=[C:11]([CH3:14])[N:12]=2)[CH:7]=[CH:6][C:5]1=[O:16])=[S:20]Participants
4
Procedure
A mixture of the free base of 1-(2-aminoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-one (700 mg., 0.0032 mole) as prepared in Example 12 and methyl isothiocyanate (180 mg., 0.004 mole) in 5 ml. of water is heated at reflux for 30 minutes. On cooling the reaction, the product is collected by filtration. After recrystallization from methanol, 1-{2-[(N-methylthiocarbamoyl)amino]ethyl}-5,7-dimethyl-1,8-naphthyridin-2(1H)-one m.p. 216.5-218° C. is obtained.