[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]=[C:12]=[S:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH2:14]([NH2:17])[CH2:15][NH2:16].O>CCOCC>[NH2:16][CH2:15][CH2:14][NH:17][C:12]([NH:11][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[S:13]A slurry of 9.75 g (0.05 mole) of 3,5-dimethoxyphenyl isothiocyanate in 27 ml of ether was added dropwise to a stirred solution of 3.0 g (0.05 mole) of ethylenediamine at room temperature. A five-degree rise in temperature was noted at the start of the one hour addition period. A solid appeared during the addition, and stirring was continued for 2.5 hours. The batch was allowed to stand overnight, and 100 ml of H2O was added. The solid was removed by filtration and the filtrate acidified with 4.5 ml of concentrated HCl and evaporated to dryness on the steam bath. The residue was sonicated with 100 ml of water and warmed to 50° C. for 10 minutes. This was filtered and basified to pH 10 with 10% NaOH. This gave 2.6 g of 14, m.p. 125°-126° C. Analysis satisfactory for C11H17N3O2S.
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