HCID 57355799, compound → Phthalimide
Reaction equation
[N-]=C=S.N1CCC(N2C3C=CC=CC=3N(CCC[N:22]3[C:26](=[O:27])[C:25]4=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]4[C:23]3=[O:32])C2=O)CC1>C(Cl)Cl.O>[C:26]1(=[O:27])[NH:22][C:23](=[O:32])[C:24]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]12Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Di(2-pyridyl)thionocarbonate (0.286 g, 1.2 mM) was added to a cold (0° C.) solution of 1,1-di(p-anisyl)methyl amine (0.3 g, 1.2 mM) and triethylamine (0.17 ml) in methylene chloride (10 ml). The resulting mixture was slowly warmed up to RT over a 4 hour period then stirred at RT for additional 1 hour to provide the 1,1-di(p-anisyl)methyl isothiocyanate. The prepared isothiocyanate was added to Compound 53 (0.94 g, 0.43 mM), prepared in Example 53, dissolved in methylene chloride (10 ml). The mixture was stirred at RT overnight, diluted with water (20 ml) and the layers were separated. The aqueous layer was again extracted with methylene chloride (2×20 ml). The combined CH2Cl2 extracts were dried over MgSO4, evaporated in vacuo and chromatoraphed (EM silica gel 60, 10% EtOAc in CH2Cl2) to give the pthalimide intermediate. This intermediate, substituted for Compound 54, was treated as described in Example 55 to give the HCl salt of the product. m/z (MH+) 560