Реакция #47722

Уравнение реакции

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

Выход 49.9%

Растворители

—

hexanes

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Другоеthe flask was placed in an oil bath
3. 3
   ТемператураThe reaction was heated to 60 C for approximately 3 hrs
4. 4
   workup.ADDITIONwere added
5. 5
   ДругоеThe resulting solids were removed by filtration
6. 6
   ПромывкаThe aqueous layer was washed with warm hexanes
7. 7
   ФильтрацияThe resulting solids were filtered from the hexane layer
8. 8
   Другоеrecrystallized
9. 9
   Температураfrom warm hexanes

Методика

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.

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