The title compound, (I), is an important intermediate in the preparation of hindered light stabilizers (Borzatta & Carrozza, 1991;Deng et al., 2006).
There are four molecules of (I) in the asymmetic unit, with simplar conformations, although two of the molecules show disorder of their tert-butyl groupings. In each case, the triazine ring is essentially planar (Fig. 1). The molecules are linked by strong, near-linear, intermolecular N-HโขโขโขN hydrogen bonds (Table 1).
Experimental
The title compound was prepared according to the method of Kaiser & Thurston (1951). 2,4,6-Trichloro-1,3,5-triazine (20.0 g, 0.109 mol) was dissolved in toluene (65 ml) and then cooled to 278 K. With stirring, a solution of 2,4,4-trimethylpentan-2-amine (13.75 g, 0.107 mol) in toluene (35 ml) was then added dropwise to the mixture over a period of 30 min. Then, a solution of Na 2 CO 3 (11.51 g, 0.109 mol) in water (30 ml) was then added dropwise for 30 min. The mixture was stirred at 273-278 K for a further 3 h and phenylmethanamine (11.61 g, 0.109 mol) and solid Na 2 CO 3 (11.51 g, 0.109 mol) were added to the mixture, maintaining the temperature at 358 K for 4.5 h. The organic layer was washed with water and then concentrated in vacuo. The title compound (28.47 g) was obtained in powder form in a yield of 75.4%. Colourles blocks (I) were obtained by slow evaporation of a solution of methanol (m.p. 421-423 K).
Refinement
The N-bound H atoms were located in a difference map and their positions and U iso values were freely refined.
The C-bound H atoms were positioned geometrically (C-H = 0.98-0.99 ร
), and refined as riding with U iso (H) = 1.2U eq (C) or 1.5U eq (methyl C).