Reaction #543537

Reaction equation

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

Yield 49.9%

Solvents

—

hexanes

water

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherthe flask was placed in an oil bath
3. 3
   TemperatureThe reaction was heated to 60 C
4. 4
   Temperaturecooled to 47 C
5. 5
   OtherThe resulting solids were removed by filtration
6. 6
   WashThe aqueous layer was washed with warm hexanes
7. 7
   FiltrationThe resulting solids were filtered from the hexane layer
8. 8
   Otherrecrystallized
9. 9
   Temperaturefrom warm hexanes

Procedure

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.

Source