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Water → 3-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

HRID 230845
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HRID 230845 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[NH:11])[NH:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:14](OC)(=O)[CH3:15].O>O1CCCC1>[CH3:14][C:15]1[O:10][N:9]=[C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[NH2:1])[N:11]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 6584Methyl AcetateHCID 24758Sodium hydrideHCID 178513310HCID 178513310, 화합물

생성물 1

HCID 114238693-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

To a stirred solution of Intermediate 18 (5.3 g) in dry tetrahydrofuran (50 ml) was added 4 Å molecular sieves, followed by sodium hydride (60% dispersion in mineral oil; 1.5 g) and the mixture heated at 65° C. for 30 min. After cooling to room temperature methyl acetate (2.8 ml) was added and the mixture heated under reflux for 16 h. After cooling to 20° C. the mixture was added to water (100 ml) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with dichloromethane to give the title compound as a white solid (4.0 g).

후처리

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 16 h
  4. temperatureAfter cooling to 20° C. the mixture
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-2e4fa84e52b04087a56901db2ef8c3c9
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07566786B2

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