Iodine → N-(2-acetyl-4-iodo-5-phenyl-pyrazol-3-yl)acetamide

HRID 1615713ノート

反応式

HRID 1615713 の反応式
[C:1]([N:4]1[C:8]([NH:9][C:10](=[O:12])[CH3:11])=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)(=[O:3])[CH3:2].[I:19](O)(=O)=O.II>C(O)C>[C:1]([N:4]1[C:8]([NH:9][C:10](=[O:12])[CH3:11])=[C:7]([I:19])[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 807IodineHCID 24345Iodic acidHCID 86717295N-(2-acetyl-5-phenyl-pyrazol-3-yl)acetamide

生成物 1

HCID 86717296N-(2-acetyl-4-iodo-5-phenyl-pyrazol-3-yl)acetamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

A suspension of N-(2-acetyl-5-phenyl-pyrazol-3-yl)acetamide (25.1 g, 0.103 mol), iodic acid (4.5 g, 0.026 mol) and iodine (15.7 g, 0.062 mol) in ethanol (250 mL) was heated at 50° C. for 3 h and cooled to room temperature. The reaction mixture was concentrated in vacuo and partitioned between CH2Cl2 and 2 M Na2S2O3 aq. solution. The layers were separated and the organic washed with brine, dried (phase separator cartridge), and concentrated in vacuo to provide a mixture of the title compound and starting material (2.2:1, 30.3 g). The mixture was put in reaction again using iodic acid (1.6 g, 9.6 mmol) and iodine (9.7 g, 38 mmol) in ethanol (250 mL) under the same conditions, to provide the title compound as a solid (31.9 g).

後処理

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between CH2Cl2 and 2 M Na2S2O3 aq. solution
  4. customThe layers were separated
  5. washthe organic washed with brine
  6. customdried (phase separator cartridge)
  7. concentrationconcentrated in vacuo
  8. customto provide

出典と根拠

ORDレコード
ord-ddf429445601449d87da5997f6d36dde
出典データセット
uspto-grants-2014_07
特許番号
US08765762B2

反応ノート

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