Reacción #1579

Ecuación de reacción

1-(5-amino-2-chloro-4-fluorophenyl)-3-(2-propynyl)-s-triazine-2,4,6-(1H,3H,5H)-trione

3,4,5,6-tetrahydrophthalic anhydride

ethyl acetate

→

title product

Rendimiento 55.9%

N-{4-Chloro-2-fluoro-5-[hexahydro-2,4,6-trioxo-3-(2-propynyl)-s-triazin-1-yl]phenyl}-1-cyclohexene-1,2-dicarboximide

Rendimiento 55.9%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled
2. 2
   LavadoThe organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   Otroto obtain a yellow semi-solid

Procedimiento

A solution of 1-(5-amino-2-chloro-4-fluorophenyl)-3-(2-propynyl)-s-triazine-2,4,6-(1H,3H,5H)-trione (1.50 g, 4.83 mmol), and 3,4,5,6-tetrahydrophthalic anhydride (0.73 g, 4.83 mmol) in acetic acid (3 mL) is heated at 100° C. for 5 hours, cooled, and poured into ethyl acetate, The organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a yellow semi-solid. Flash column chromatography of the semi-solid using silica gel and an ethyl acetate/hexanes (1:2) solution gives the title product as a white solid (1.20 g, mp 127°-135° C.).

Fuente