Potassium Carbonate → 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone

HRID 1199617

반응식

HRID 1199617 반응식
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[N:24]=[C:23]([CH3:25])[O:22][N:21]=1>C(#N)C>[F:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([CH2:19][C:20]3[N:24]=[C:23]([CH3:25])[O:22][N:21]=3)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 446672-Benzothiazolinone, 6-fluoro-HCID 3021573-(Chloromethyl)-5-methyl-1,2,4-oxadiazole

생성물 1

HCID 199794996-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone수율 91.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 6-fluoro-2(3H)-benzothiazolone (8.45 g), acetonitrile (100 ml) and potassium carbonate (7.6 g) was prepared. To this mixture was added dropwise 3-chloromethyl-5-methyl-1,2,4-oxadiazole (7.3 g) at a temperature of 40° to 50° C. under stirring. The reaction mixture was heated under refluxing for 5 hours. The reaction mixture was then cooled and filtered. The filtrate was distilled under a reduced pressure, and the residue was admixed with ethyl acetate (200 ml) and water (100 ml). The resultant organic layer was separated and washed with a 5% aqueous potassium hydroxide solution, with water and then with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was dissolved in a minimum amount of ethanol under heating. The solution thus formed was cooled to a temperature of 0° to 5° C. to precipitate a crystalline product, which was then separated by filtration, and dried, so that the aimed compound, i.e. 6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone (12.1 g) was obtained. m.p. 142°-144° C.

후처리

  1. customwas prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureunder refluxing for 5 hours
  4. temperatureThe reaction mixture was then cooled
  5. filtrationfiltered
  6. distillationThe filtrate was distilled under a reduced pressure
  7. customThe resultant organic layer was separated
  8. washwashed with a 5% aqueous potassium hydroxide solution, with water
  9. dry with materialwith a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. dissolutionthe residue was dissolved in a minimum amount of ethanol
  12. temperatureunder heating
  13. customThe solution thus formed
  14. temperaturewas cooled to a temperature of 0° to 5° C.
  15. customto precipitate a crystalline product, which
  16. customwas then separated by filtration
  17. dry with materialdried, so that the aimed compound

출처 및 근거

ORD 기록
ord-b37db02ce37646279c0747d2377c47be
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04902335

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