Iodine → 3-(2,5-dimethylpyrrol-1-yl)-5-iodo-1-phenyl-1H-pyrazole

HRID 83489ノート

反応式

HRID 83489 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.C([Li])CCC.[I:24]I.S([O-])(O)=O.[Na+]>O1CCCC1.O>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[C:11]([I:24])[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 807IodineHCID 23665763Sodium BisulfiteHCID 712878563-(2,5-Dimethylpyrrol-1-yl)-1-phenyl-1H-pyrazoleHCID 178418339Butyllithium

生成物 1

HCID 866803513-(2,5-dimethylpyrrol-1-yl)-5-iodo-1-phenyl-1H-pyrazole収率 58.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3-(2,5-dimethylpyrrol-1-yl)-1-phenyl-1H-pyrazole (14.6 g) in tetrahydrofuran (80 ml) cooled to −78° C. was added n-butyllithium (1.6M solution in n-hexane, 24 ml) over 5 minutes, and then the mixture was stirred for 1 hour. To this mixture was added a solution of iodine (15.7 g) in tetrahydrofuran (30 ml) over 10 minutes, and the mixture was stirred for additional 1.5 hours. To this mixture were sequentially added water (5 ml) and a saturated aqueous solution of sodium hydrogen sulfite (30 ml), and then the mixture was warmed to 0° C., and additional water (150 ml) was added thereto, and the mixture was stirred at room temperature for 1 hour. A precipitated solid was collected by filtration, washed with water and a small amount of methanol, and dried under reduced pressure to give the titled compound (13.0 g).

後処理

  1. stirringthe mixture was stirred for additional 1.5 hours
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationA precipitated solid was collected by filtration
  4. washwashed with water
  5. dry with materiala small amount of methanol, and dried under reduced pressure

出典と根拠

ORDレコード
ord-bec92af3cad5469eacdf46a5dec791a5
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

反応ノート

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