تفاعل #543537

معادلة التفاعل

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

المردود 49.9%

المذيبات

—

hexanes

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   أخرىthe flask was placed in an oil bath
3. 3
   درجة الحرارةThe reaction was heated to 60 C
4. 4
   درجة الحرارةcooled to 47 C
5. 5
   أخرىThe resulting solids were removed by filtration
6. 6
   غسيلThe aqueous layer was washed with warm hexanes
7. 7
   ترشيحThe resulting solids were filtered from the hexane layer
8. 8
   أخرىrecrystallized
9. 9
   درجة الحرارةfrom warm hexanes

الإجراء التجريبي

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.

المصدر