Sodium Hydroxide → 3-(4-Phthalimidobutylthio)pyridine

HRID 2210097

반응식

HRID 2210097 반응식
CN(N[C:5]([S:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=O)C.[OH-].[Na+].BrC[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31]>CO>[C:22]1(=[O:31])[N:21]([CH2:20][CH2:19][CH2:18][CH2:5][S:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]12

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 93575N-(4-Bromobutyl)phthalimideHCID 190790823-Dimethylaminocarbamoylthiopyridine

생성물 1

HCID 190791033-(4-Phthalimidobutylthio)pyridine수율 4.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 3.64 g (20 mmol) of 3-dimethylaminocarbamoylthiopyridine in 100 ml of methanol was added 1.6 g (40 mmol) of sodium hydroxide. The mixture was heated and refluxed for 3 hours under nitrogen atmosphere. After cooling, 5.64 g (20 mmol) of N-(4-bromobutyl)phthalimide was added. The mixture was heated and refluxed for 2.5 hours. The solvent was distilled off and chloroform was added to the residue. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=1:1) to obtain 280 mg of the desired compound (4.5%, colorless oil).

후처리

  1. temperatureThe mixture was heated
  2. temperaturerefluxed for 3 hours under nitrogen atmosphere
  3. temperatureAfter cooling
  4. temperatureThe mixture was heated
  5. temperaturerefluxed for 2.5 hours
  6. distillationThe solvent was distilled off
  7. additionchloroform was added to the residue
  8. washThe mixture was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customthe residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=1:1)

출처 및 근거

ORD 기록
ord-12c1971be46649e3a2e53a40ac305536
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05457106

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