Dichloromethane → 2,5-Di(4-pyridyl)-4-methylthiophen-3-ylmethylhydroxylamine trihydrochloride
Reaction equation
C(OC([N:8]([CH2:17][C:18]1[C:22]([CH3:23])=[C:21]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[S:20][C:19]=1[C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)[O:9]C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+].C(Cl)[Cl:49]>>[ClH:49].[ClH:49].[ClH:49].[N:33]1[CH:34]=[CH:35][C:30]([C:19]2[S:20][C:21]([C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)=[C:22]([CH3:23])[C:18]=2[CH2:17][NH:8][OH:9])=[CH:31][CH:32]=1Participants
5
Procedure
To a stirred solution of N,O-di-tert-butoxycarbonyl-[2,5-di(4-pyridyl)-4-methylthiophen-3-yl]methylhydroxylamine (0.16 g) in CH2Cl2 (15 mL) was added trifluoroacetic acid (0.5 mL) and the mixture watered for 2 hours at room temperature. Trifluoroacetic acid (3 mL) was additionally added to the reaction mixture, and stirred for 2 hours. Saturated aqueous NaHCO3 solution was added to the reaction mixture and the whole was extracted with CH2Cl2 (100 mL×2). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-CH2Cl2 (1:1). The crude product was dissolved in 10% methanolic HCl (1 mL) and the volatiles were removed by evaporation. The resulting solid was recrystallized from diisopropyl ether to give the title compound (0.031 g).