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

HRID 64970노트

반응식

HRID 64970 반응식
[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=12.[P:20](Cl)([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(=O)([O-])[O-]>CN(C=O)C.C(OCC)(=O)C>[P:20]([O:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=12)([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21]

참가 물질

8

반응물 5

HCID 4875Potassium Iodide2회HCID 11430Potassium Carbonate2회HCID 13139Diethyl chlorophosphate2회HCID 19660Carbonate Ion2회HCID 137124785-hydroxy-12H-benzo[a]phenothiazine

생성물 1

HCID 13712499Diethyl 12H-benzo[a]phenothiazin-5-yl phosphate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  1. stirringstirring
  2. stirringThe mixture was stirred for 3 days
  3. filtrationthe insolubles filtered
  4. washThe filtrate was washed with water
  5. customdried
  6. customevaporated down
  7. customThis residue was crystallized from acetone
  8. customchromatographed on a column of silica gel
  9. washeluting first with 1:1

출처 및 근거

ORD 기록
ord-b19ed31449ef4fa6856a3ace05b8b6b6
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04611056

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