Pyridine → 1,5-bis(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole

HRID 584725

반응식

HRID 584725 반응식
[F:1][C:2]([F:16])([F:15])[C:3](=[N:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[NH2:4].N1C=CC=CC=1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=O)=[CH:27][CH:26]=1>O1CCOCC1>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:29]([C:28]3[CH:32]=[CH:33][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)=[N:4][C:3]([C:2]([F:15])([F:16])[F:1])=[N:5]2)=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 696776222,2,2-trifluoro-N'-(4-methoxyphenyl)ethanehydrazonamide

생성물 1

HCID 102914551,5-bis(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole수율 48.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

To a solution of 2,2,2-trifluoro-N′-(4-methoxyphenyl)ethanehydrazonamide (0.92 g, 3.95 mmol) in 10 mL of dioxane, were added pyridine (0.319 mL, 3.95 mmol) and a solution of 4-methoxybenzoyl chloride (673 mg, 3.95 mmol) in 3 mL of dioxane. The mixture was refluxed with stirring for 12 hours. The solvent was removed under reduced pressure. 50 mL of dichloromethane and 20 mL of 0.1 N hydrochloric acid were added to the residue and the organic layer was separated. The aqueous layer was extracted with 50 mL of dichloromethane. A combined organic layer was washed with 0.1 N hydrochloric acid and brine and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (toluene-ethyl acetate 9:1) and then recrystallized with diisopropyl ether-hexane to give pale brown needle of 1,5-bis(4-methoxyphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (0.67 g, 48.6% yield).

후처리

  1. temperatureThe mixture was refluxed
  2. customThe solvent was removed under reduced pressure
  3. addition50 mL of dichloromethane and 20 mL of 0.1 N hydrochloric acid were added to the residue
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with 50 mL of dichloromethane
  6. washA combined organic layer was washed with 0.1 N hydrochloric acid and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (toluene-ethyl acetate 9:1)
  10. customrecrystallized with diisopropyl ether-hexane

출처 및 근거

ORD 기록
ord-8c802859d6794e89b1ed4ca9ec73cd50
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927230B2

연결된 노트

불러오는 중…