2,4-Dichloro-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-1,3,5-triazine

The title compound, C13H11Cl2N3O2, was obtained by the reaction of eugenol and cyanuric chloride. The dihedral angle between the benzene and triazine rings is 87.56 (4)°. Two C atoms of the allyl group are disordered over two sites in a 0.72 (2):0.28 (2) ratio.

The title compound, C 13 H 11 Cl 2 N 3 O 2 , was obtained by the reaction of eugenol and cyanuric chloride. The dihedral angle between the benzene and triazine rings is 87.56 (4) . Two C atoms of the allyl group are disordered over two sites in a 0.72 (2):0.28 (2) ratio.

Related literature
For background to the Williamson reaction in organic synthesis, see: Dermer (1934). For related structures, see: Ma et al.(2010a,b,c). For agricultural applications of the title compound, see: Manning et al. (1987).

Comment
In this paper, we used the Williamson reaction (Dermer, 1934) to form the title compound, (I), which was synthesized by the reaction of eugenol, sodium hydroxide and cyanuric chloride at 278 K. We have previously reported three compounds of this type [Ma et al.(2010a[Ma et al.( , 2010b[Ma et al.( and 2010c]. In (I) (Fig.1), the dihedral angle between the benzene ring C4-C9 and the triazine ring C2N3C3N1C1N2 is 87.56 (4)°. There are no significantly short intermolecular contacts in the crystal lattice.
Experimental 492 mg eugenol (3 mmol) was dissolved in 1.2 g 10% sodium hydroxide (3 mmol) in a 100 mL round-bottom flask and the water was then removed in vacuo. Added 30 ml acetonitrile into the flask in an ice bath and after stirring 10 min cyanuric chloride (3 mmol) was added and kept stirred for 2 h at 278 K. The reaction mixture was filtered and solvent was evaporated under vacuum to dryness. The solid mass was dissolved in EtOAc, washed with saturated NaHCO 3 and brine, dried over anhydrous Na 2 SO 4 , concentrated and purified with column chromatography to afford the crude product. White crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the title compound in n-hexane/ethyl acetate

Refinement
The atoms C12 and C13 were found to be disordered over two sites, and the ratio of the occupancy factors refined to 0.718 (7):0.282 (7) and 0.718 (7):0.282 (7) for atoms C12: C12' and C13: C13' respectively.The positions of all H atoms were determined geometrically and refined using a riding model with C-H = 0.93-0.97 Å and U iso (methyl H) = 1.5U eq (C) and 1.2U eq for other H atoms. Fig. 1. The molecular structure of (I), with atom labels and displacement ellipsoids drawn at the 30% probability level.The disordered atoms C12 and C13 of the allyl group are the major component.