1H-1,2,4-Triazole → 1-(3-fluoro-4-nitrophenyl)-1H-1,2,4-triazole

HRID 2299205

반응식

HRID 2299205 반응식
[F:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

참가 물질

6

반응물 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

생성물 1

HCID 218839191-(3-fluoro-4-nitrophenyl)-1H-1,2,4-triazole수율 50.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

2,4-Difluoronitrobenzene (8.0 g) was dissolved in N,N-dimethylformamide (110 ml) and the solution was admixed with 1H-1,2,4-triazole (3.47 g) and potassium carbonate (6.95 g) and the mixture was stirred under a nitrogen atmosphere at 70° C. for 20 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the ethyl acetate layers were combined and washed 5 times with water and then with saturated brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:1.3). A desired fraction was concentrated under reduced pressure and the residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to yield 1-(3-fluoro-4-nitrophenyl)-1H-1,2,4-triazole (5.29 g) as yellow powdery crystals.

후처리

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washwashed 5 times with water
  4. dry with materialwith saturated brine, and then dried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:1.3)
  7. concentrationA desired fraction was concentrated under reduced pressure
  8. customthe residue was crystallized from a mixture of ethyl acetate and diisopropyl ether

출처 및 근거

ORD 기록
ord-ecb7d74152ca42e6b877fbad88b73f12
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495604B1

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