2-Fluoroaniline → 3-Benzyloxymethyl-5-biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazole

HRID 6935

반응식

HRID 6935 반응식
[CH2:1]([O:8][CH2:9][C:10]([NH:12][NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[F:33][C:34]1[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=1[NH2:36]>C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C:10]1[N:36]([C:35]2[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=2[F:33])[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[N:13][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 95842-FluoroanilineHCID 24813Phosphorus oxychlorideHCID 69584562biphenyl-4-carboxylic acid N'-(2-benzyloxyacetyl) hydrazide

생성물 1

HCID 220192303-Benzyloxymethyl-5-biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazole수율 58%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To biphenyl-4-carboxylic acid N′-(2-benzyloxyacetyl)hydrazide (9.38 g) was added phosphorus oxychloride (30 ml), and stirred at 100° C. for one hour. After the reaction solution was cooled to ambient temperature, the reaction solution was concentrated under reduced pressure. To the resulting residue was added ethyl acetate, and the separated organic layer was washed with aqueous 1 mol/liter sodium hydroxide solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to afford an oily product. Subsequently, 2-fluoroaniline (5 ml) and p-toluenesulfonic acid·monohydrate (200 mg) were added to the resulting oily product, and stirred at 140° C. for 4 hours. After the reaction solution was cooled to ambient temperature, ethyl acetate was added to the reaction solution. The separated organic layer was washed with aqueous 1 mol/liter sodium hydroxide solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=3/1–1/1), to afford the entitled compound 3-benzyloxymethyl-5-biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazole as pale yellow solid (6.60 g, 58%). The physico-chemical values are as follows.

후처리

  1. temperatureAfter the reaction solution was cooled to ambient temperature
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionTo the resulting residue was added ethyl acetate
  4. washthe separated organic layer was washed with aqueous 1 mol/liter sodium hydroxide solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customto afford an oily product
  8. stirringstirred at 140° C. for 4 hours
  9. temperatureAfter the reaction solution was cooled to ambient temperature
  10. washThe separated organic layer was washed with aqueous 1 mol/liter sodium hydroxide solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe resulting residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=3/1–1/1)

출처 및 근거

ORD 기록
ord-292a0a704b9b471094fb6636feb1e86e
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084164B2

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