2,4,6-Trimethylaniline → PhCH(CH3)NHMes

Participants

Reaction Steps

To a solution of 104 μL, (100 mg; 0.741 mmol) of mesitylamine, 136 μL, (108 mg; 0.741 mmol) t-butyl peroxide, 20 mL (neat) ethylbenzene was added the appropriate amount of {[Cl2NNF6Cu]}2(C6H6) from a stock solution in benzene. The reaction mixture was allowed to react inside a sealed pressure vessel and allowed to react at the specified temperature and time. Yields were determined via 1H NMR using 1,2,4,5-tetrachlorobenzene as a standard. See FIGS. 22 and 23. 1H NMR (benzene-d6, RT): δ 7.105 (m, 7, Ar—H), 4.159 (m, 1, CBz—H), 2.907 (br, 1, N—H), 2.142 (s, 3, p-CH3), 2.040 (s, 6, o-CH3), 1.341 (d, 3, CH3); m/z=240 (CI mode); byproduct diazene MesN═NMes 1H NMR (benzene-d6): δ 6.742 (s, 4, Ar—H), 2.461 (s, 12, o-CH3), 2.116 (s, 6, p-CH3); m/z=267 (CI mode).

Provenance & Evidence