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

HRID 64970ノート

反応式

HRID 64970 の反応式
[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]

参加物

8

反応物 5

HCID 4875Potassium Iodide2 回HCID 11430Potassium Carbonate2 回HCID 13139Diethyl chlorophosphate2 回HCID 19660Carbonate Ion2 回HCID 137124785-hydroxy-12H-benzo[a]phenothiazine

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b19ed31449ef4fa6856a3ace05b8b6b6
出典データセット
uspto-grants-1986_09
特許番号
US04611056

反応ノート

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