Reacción #543537

Ecuación de reacción

6-chloro-2H-1,3-benzoxazine-2,4(3H)-dione

DMF

1,10-dibromodecane

DMF

Diisopropylethylamine

→

6-chloro-3-(10-bromodecyl)-2H-1,3-benzoxazine-2,4(3H)-dione

Rendimiento 49.9%

Disolventes

—

hexanes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Otrothe flask was placed in an oil bath
3. 3
   TemperaturaThe reaction was heated to 60 C
4. 4
   Temperaturacooled to 47 C
5. 5
   OtroThe resulting solids were removed by filtration
6. 6
   LavadoThe aqueous layer was washed with warm hexanes
7. 7
   FiltraciónThe resulting solids were filtered from the hexane layer
8. 8
   Otrorecrystallized
9. 9
   Temperaturafrom warm hexanes

Procedimiento

A slurry of 9.77 g of 6-chloro-2H-1,3-benzoxazine-2,4(3H)-dione (50 mmol) and 60 ml of DMF was treated with a solution of 1,10-dibromodecane (52.52 g, 0.175 mol) and DMF (60 ml) was added. Diisopropylethylamine (9.6 ml, 55 mmol) was added dropwise. A thermometer and condenser were attached, and the flask was placed in an oil bath. The reaction was heated to 60 C. for approximately 3 hrs, cooled to 47 C. and hexanes (150 ml) were added. The mixture was diluted with water (175 ml). The resulting solids were removed by filtration. The aqueous layer was washed with warm hexanes. The resulting solids were filtered from the hexane layer and recrystallized from warm hexanes to give 10.39 g of 6-chloro-3-(10-bromodecyl)-2H-1,3-benzoxazine-2,4(3H)-dione.

Fuente