Réaction #50448

Équation de réaction

2-chloro-4,6-dimethoxy-1,3,5-triazine

7-hydroxy-3-methyl-isobenzofuran-1(3H)-thione

sodium hydride

hydrogen

→

7-[(4,6-dimethoxy-1,3,5-triazin-2-yl)oxy]-3-methyl-isobenzofuran-1(3H)-thione

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionthe whole is extracted with ethyl acetate
2. 2
   Lavagewashed with sodium chloride solution
3. 3
   ConcentrationThe crude product, having been concentrated by evaporation
4. 4
   Autreis purified by chromatography (eluant: 45% ethyl acetate in n-hexane)
5. 5
   Autrerecrystallised from acetone/n-hexane

Mode opératoire

1.0 g of 7-hydroxy-3-methyl-isobenzofuran-1(3H)-thione is introduced into a suspension of 0.15 g of sodium hydride in absolute dimethylformamide and, when the evolution of hydrogen has ceased, 1.0 g of 2-chloro-4,6-dimethoxy-1,3,5-triazine is added thereto. The reaction mixture is subsequently stirred at room temperature for 5 hours, ice-water is then added and the whole is extracted with ethyl acetate and washed with sodium chloride solution. The crude product, having been concentrated by evaporation, is purified by chromatography (eluant: 45% ethyl acetate in n-hexane) and recrystallised from acetone/n-hexane to yield 7-[(4,6-dimethoxy-1,3,5-triazin-2-yl)oxy]-3-methyl-isobenzofuran-1(3H)-thione in the form of yellow crysals, m.p. 177°-178° C.; IR spectrum (CHCl3): 1590, 1560, 1366, 1304, 1140 cm-1 ; 1H-NMR (CDCl3): 5.81 ppm (q, 1H), 1.73 ppm (d, 3H).

Source