Sodium Chloride → 1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carbonitrile

HRID 475500ノート

反応式

HRID 475500 の反応式
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]([NH2:11])=O)=[N:2]1.[Cl-].[Na+].P(Cl)(Cl)(Cl)=O>C(#N)C>[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]#[N:11])=[N:2]1

参加物

5

反応物 3

HCID 5234Sodium ChlorideHCID 24813Phosphorus oxychlorideHCID 451212581H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxamide

生成物 1

HCID 231351391H,4H,5H,6H-cyclopenta[c]pyrazole-3-carbonitrile

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

1,4,5,6-Tetrahydro-cyclopentapyrazole-3-carboxylic acid amide (0.210 g, 1.39 mmol) was added to anhydrous acetonitrile (12 cm3), heated to 80° C. and sodium chloride (2.0 g, 34-mmol) added. After 15 minutes phosphorus oxychloride (0.128 g, 0.83 mmol) was added and the solution heated to 80° C. overnight, cooled, filtered, and the collected solid washed with acetonitrile. Solvent was removed from the combined solutions under reduced pressure and the resulting solid purified by preparative HPLC to give 1,4,5,6-tetrahydro-cyclopentapyrazole-3-carbonitrile as a deep purple coloured solid (0.031 g, 0.23 mmol, 17%). δH (CD3OD): 2.79 (t like, 2H, J=7.3), 2.73 (t like, 2H, J=7.1), 2.65-2.55 (m, 2H); m/z (ES+): 134 [M+H]+.

後処理

  1. temperaturethe solution heated to 80° C. overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. washthe collected solid washed with acetonitrile
  5. customSolvent was removed from the combined solutions under reduced pressure
  6. customthe resulting solid purified by preparative HPLC

出典と根拠

ORDレコード
ord-b715a3541ca34ee298e9497ac23a7e2f
出典データセット
uspto-grants-2014_01
特許番号
US08637555B2

反応ノート

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