Реакция #93248

Уравнение реакции

5-hydroxy-12H-benzo[a]phenothiazine

diethyl chlorophosphate

potassium carbonate

potassium iodide

carbonate

potassium carbonate

potassium iodide

carbonate

diethyl chlorophosphate

→

title compound

Diethyl 12H-benzo[a]phenothiazin-5-yl phosphate

Растворители

ethyl acetate

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   workup.STIRRINGThe mixture was stirred for 3 days
3. 3
   Фильтрацияthe insolubles filtered
4. 4
   ПромывкаThe filtrate was washed with water
5. 5
   Другоеdried
6. 6
   Другоеevaporated down
7. 7
   ДругоеThis residue was crystallized from acetone
8. 8
   Другоеchromatographed on a column of silica gel
9. 9
   Промывкаeluting first with 1:1

Методика

To a solution of 5-hydroxy-12H-benzo[a]phenothiazine (1.5 g) and diethyl chlorophosphate (2 ml) in DMF (20 ml) there was added a powdered mixture of potassium carbonate (2 g) and potassium iodide (2 g). The reaction mixture was stirred at room temperature. After 30 minutes, a further addition of potassium carbonate and potassium iodide (2 g each) was made and stirring was continued. Two hours later more carbonate (2 g) and diethyl chlorophosphate (2 ml) were added, and then three hours later a final addition of carbonate (2 g) was made. The mixture was stirred for 3 days then diluted with ethyl acetate (60 ml) and the insolubles filtered. The filtrate was washed with water, dried and evaporated down. This residue was crystallized from acetone, then chromatographed on a column of silica gel, eluting first with 1:1, then 3:1 mixtures of ethyl acetate and hexane to afford pure title compound (337 mg), m.p. 162°-163° C.

Источник