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1H-1,2,4-Triazole → 1,1-bis(5-chloropyrid-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol

HRID 371181
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HRID 371181 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=3)[CH2:10][O:9]2)=[N:6][CH:7]=1.[NH:18]1[CH:22]=[N:21][CH:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)([OH:9])[CH2:10][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)=[N:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 202745202,2-Bis(5-chloro-pyrid-2-yl)oxirane

생성물 1

HCID 202745161,1-bis(5-chloropyrid-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol수율 47.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

2,2-Bis(5-chloro-pyrid-2-yl)oxirane (0.8 g), 1,2,4-triazole (1.0 g) and anhydrous potassium carbonate (3.0 g) were stirred in dry N,N-dimethylformamide (30 ml) and the mixture was heated at 85° C. for 1.5 hours. The solvent was then evaporated under vacuum, with the addition of xylene to remove final traces of N,N-dimethylformamide as an azeotrope, and the residue was dissolved in water (20 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried over megnesium sulfate and evaporated. The residue was chromatographed on silica, eluting with ethyl acetate. Evaporation of the relevant fractions gave a viscous oil which solidified on trituration with petroleum ether (b.p. 60°-80° C.). Recrystallization from hexane gave the title compound as white crystals (0.48 g, 38%) m.p. 98°-100° C.

후처리

  1. customThe solvent was then evaporated under vacuum, with the addition of xylene
  2. customto remove final traces of N,N-dimethylformamide as an azeotrope
  3. dissolutionthe residue was dissolved in water (20 ml)
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined organic extracts were dried over megnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica
  8. washeluting with ethyl acetate
  9. customEvaporation of the relevant fractions
  10. customgave a viscous oil which
  11. customRecrystallization from hexane

출처 및 근거

ORD 기록
ord-c02b2df88220435082c29a8f87cc9513
출처 데이터셋
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04529799

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