Azobisisobutyronitrile → 4-(azidomethyl)-1-(4-iodophenyl)-1H-pyrazole

HRID 643028노트

반응식

HRID 643028 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C1C(=O)N(Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[N-:34]=[N+:35]=[N-:36].[Na+]>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O.O>[N:34]([CH2:13][C:11]1[CH:10]=[N:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)[CH:12]=1)=[N+:35]=[N-:36]

참가 물질

8

반응물 4

HCID 6547AzobisisobutyronitrileHCID 33557Sodium AzideHCID 67184N-bromobutanimideHCID 685096071-(4-iodophenyl)-4-methyl-1H-pyrazole

생성물 1

HCID 866140084-(azidomethyl)-1-(4-iodophenyl)-1H-pyrazole수율 35.9%

시약·촉매·용매 3

HCID 962Water용매HCID 5943Carbon Tetrachloride용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1-(4-iodophenyl)-4-methyl-1H-pyrazole (1.70 g, 5.99 mmol), NBS (1.38 g, 7.75 mmol) and AIBN (0.30 g, 1.83 mmol) in CCl4 (25 mL) was heated at reflux for 1 hr. After being cooled to room temperature, the upper clear solution was decanted out and concentrated in vacuo. The residue was dissolved in DMF (10 mL), NaN3 (0.934 g, 14.3 mmol) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with hexane, then with 5% EtOAc in hexane to give 4-(azidomethyl)-1-(4-iodophenyl)-1H-pyrazole (0.70 g).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 1 hr
  3. customthe upper clear solution was decanted out and
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in DMF (10 mL)
  6. customThe organic phase was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by a silica gel column
  10. washeluted with hexane

출처 및 근거

ORD 기록
ord-fe1888e3a3de49fe905c175f850b07e2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696352B2

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