Ethanol → 3-(2-hydroxy-3-morpholinopropyl)-1H-2,3-benzothiazin-4(3H)-one 2,2-dioxide

HRID 964946

반응식

HRID 964946 반응식
[Na].[CH2:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[NH:4][S:3]1(=[O:14])=[O:13].Cl[CH2:16][CH:17]([OH:25])[CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[CH2:26]([OH:28])[CH3:27]>>[OH:25][CH:17]([CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[CH2:16][N:4]1[C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:2][S:3]1(=[O:13])=[O:14].[CH2:26]([O:28][CH:17]([CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[CH2:16][N:4]1[C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:2][S:3]1(=[O:13])=[O:14])[CH3:27]

참가 물질

6

반응물 4

HCID 702EthanolHCID 890421H-2,3-Benzothiazin-4(3H)-one 2,2-dioxideHCID 5360545SodiumHCID 100809871-Chloro-3-morpholin-4-yl-propan-2-ol

생성물 2

HCID 190743823-(2-ethoxy3-morpholinopropyl)-1H-2,3-benzothiazin-4(3H)-one 2,2-dioxide수율 20%HCID 190744153-(2-hydroxy-3-morpholinopropyl)-1H-2,3-benzothiazin-4(3H)-one 2,2-dioxide수율 63%

반응 조건

온도
50 °C

실험 절차

In dry ethanol (10 mL) was dissolved metallic sodium (23 mg, 1 mmol.), and to the solution was added 1H-2,3-benzothiazin-4(3H)-one 2,2-dioxide (197 mg, 1 mmol.). The mixture was stirred at 50° C. for 30 min. To the reaction solution was added 1-chloro-3-morpholino-2-propanol (198 mg, 1.1 mmol.). The mixture was then heated for 6 hours under refluxing. The reaction liquid was placed under reduced pressure to distill the solvent off. The resulting residue was treated with 1N hydrochloric acid and ethyl acetate. The aqueous layer was taken out, and made basic by addition of potassium carbonate. The oil precipitated and was extracted with ethyl acetate. The ethyl acetate portion was washed with an aqueous saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The dried ethyl acetate portion was placed under reduced pressure to distill the solvent off. The resulting residue was treated by silica gel column chromatography (chloroform/methanol=40/1) to give 3-(2-hydroxy-3-morpholinopropyl)-1H-2,3-benzothiazin-4(3H)-one 2,2-dioxide (215 mg, yield 63%) as a colorless oil, and 3-(2 -ethoxy3-morpholinopropyl)-1H-2,3-benzothiazin-4(3H)-one 2,2-dioxide (70 mg, yield 20%) as an colorless oil.

후처리

  1. temperatureThe mixture was then heated for 6 hours
  2. temperatureunder refluxing
  3. customThe reaction liquid
  4. distillationto distill the solvent off
  5. additionThe resulting residue was treated with 1N hydrochloric acid and ethyl acetate
  6. additionmade basic by addition of potassium carbonate
  7. customThe oil precipitated
  8. extractionwas extracted with ethyl acetate
  9. washThe ethyl acetate portion was washed with an aqueous saturated sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationto distill the solvent off
  12. additionThe resulting residue was treated by silica gel column chromatography (chloroform/methanol=40/1)

출처 및 근거

ORD 기록
ord-453b986b65ad4d428d6cef8b43f374de
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773437

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