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

HRID 643028ノート

反応式

HRID 643028 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 5943Carbon Tetrachloride溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fe1888e3a3de49fe905c175f850b07e2
出典データセット
uspto-grants-2010_04
特許番号
US07696352B2

反応ノート

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