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

HRID 475500노트

반응식

HRID 475500 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-b715a3541ca34ee298e9497ac23a7e2f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637555B2

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