Sodium Iodide → 4-bromo-1-ethyl-5-(4-phthalimidobutyl)-1H-pyrazole-3-carbonitrile

HRID 1360434

反応式

HRID 1360434 の反応式
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[I-].[Na+].[Br:15][C:16]1[C:17]([C:28]#[N:29])=[N:18][N:19]([CH2:26][CH3:27])[C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24]Cl>C(Cl)(Cl)Cl.O.CN(C=O)C>[Br:15][C:16]1[C:17]([C:28]#[N:29])=[N:18][N:19]([CH2:26][CH3:27])[C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

参加物

7

反応物 3

HCID 5238Sodium Iodide2 回HCID 24194345Phthalimide potassium salt2 回HCID 669582654-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile

生成物 1

HCID 669584184-bromo-1-ethyl-5-(4-phthalimidobutyl)-1H-pyrazole-3-carbonitrile収率 71.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
100 °C

実験手順

Potassium phthalimide (954 mg, 5.15 mmol), sodium iodide (130 mg, 0.86 mmol), and DMF (5 mL) were added to 4-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile (1.0 g, 3.4 mmol, prepared as described in Parts A-E of Example 19), and the reaction was heated at 100° C. for 45 minutes under a nitrogen atmosphere and allowed to cool to ambient temperature. Water (50 mL) was added, and the resulting mixture was stirred at 0° C. A precipitate formed, was isolated by filtration, and was dissolved in chloroform. The resulting solution was dried over sodium sulfate, filtered, and concentrated under reduced pressure. An analysis by nuclear resonance spectroscopy (NMR) indicated that starting material was present. The solid was treated with potassium phthalimide (1.27 g, 6.88 mmol), sodium iodide (130 mg, 0.86 mmol), and DMF (5 mL) and heated at 90° C. for three hours. Water (50 mL) was added, and the resulting solid was isolated by filtration to provide 0.97 g of 4-bromo-1-ethyl-5-(4-phthalimidobutyl)-1H-pyrazole-3-carbonitrile as a gray, crystalline solid.

後処理

  1. temperatureto cool to ambient temperature
  2. customA precipitate formed
  3. customwas isolated by filtration
  4. dry with materialThe resulting solution was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. temperatureheated at 90° C. for three hours
  8. customthe resulting solid was isolated by filtration

出典と根拠

ORDレコード
ord-9bfbb018d7e8437199b1c3c09ca184d7
出典データセット
uspto-grants-2011_02
特許番号
US07879849B2

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