6-phenylnicotinic acid N'-(4-methoxybutyryl)hydrazide → 5-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine

HRID 6927

반응식

HRID 6927 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][NH:9][C:10](=[O:23])[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:13][CH:12]=1)=O>P(Cl)(Cl)(Cl)=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[O:23][C:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:13][CH:12]=2)=[N:9][N:8]=1

참가 물질

3

반응물 1

HCID 695844476-phenylnicotinic acid N'-(4-methoxybutyryl)hydrazide

생성물 1

HCID 220192365-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine수율 65.1%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

반응 조건

온도
100 °C

실험 절차

To 6-phenylnicotinic acid N′-(4-methoxybutyryl)hydrazide (6.06 g) was added phosphorus oxychloride (100 ml), and stirred at 100° C. for 3 hours. After the reaction solution was cooled to ambient temperature, the solution was concentrated under reduced pressure. To the resulting residue was added aqueous 1 mol/liter sodium hydroxide solution under ice cooling, and extracted with chloroform. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1 to 1/1 to 1/2 to 1/5), and washed with a mixture solvent of n-hexane and ethyl acetate, to afford the entitled compound 5-[5-(3-methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine 3.72 g, 65%). The physico-chemicalvalues are as follows.

후처리

  1. temperatureAfter the reaction solution was cooled to ambient temperature
  2. concentrationthe solution was concentrated under reduced pressure
  3. additionTo the resulting residue was added aqueous 1 mol/liter sodium hydroxide solution under ice cooling
  4. extractionextracted with chloroform
  5. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1 to 1/1 to 1/2 to 1/5)
  8. washwashed with a mixture solvent of n-hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-27aad1f22981490b815940bdd6106842
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084164B2

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