Phosphorus oxychloride → 2-(2-Chloropyridin-3-yl)acetonitrile

HRID 751351노트

반응식

HRID 751351 반응식
[CH:1]1[CH:6]=[N+:5]([O-])[CH:4]=[C:3]([CH2:8][C:9]#[N:10])[CH:2]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:4]1[C:3]([CH2:8][C:9]#[N:10])=[CH:2][CH:1]=[CH:6][N:5]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 2431673-(Cyanomethyl)pyridin-1-ium-1-olate

생성물 1

HCID 147395432-(2-Chloropyridin-3-yl)acetonitrile수율 42.9%

반응 조건

온도
5 °C

실험 절차

(1-oxypyridin-3-yl)acetonitrile (7.5 g, 35.9 mmol) is carefully added to vigorously stirred phosphorous oxychloride (100 mL). The mixture is slowly heated to 80° C. (in 5° C. increments) over 1.5 hr. (CAUTION. If heating is too quick, violent decomposition occurs at ca 70° C.) All the solids dissolved. The reaction is heated at reflux for 3 hr. The excess phosphorous oxychloride is removed and the residue is cautiously treated with cold water. Saturated sodium bicarbonate is added to make the mixture basic, then it is extracted with ethyl acetate (3×). The combined extract is washed with brine, dried, filtered and concentrated. The residue is purified by chromatography eluting with pentane-10 to 100% ether. The second compound off the column is the desired (2-chloropyridin-3-yl)acetonitrile (2.35 g, 42.9% yield) a light brown solid.

후처리

  1. temperatureIf heating
  2. customoccurs at ca 70° C.
  3. dissolutiondissolved
  4. temperatureThe reaction is heated
  5. temperatureat reflux for 3 hr
  6. customThe excess phosphorous oxychloride is removed
  7. additionthe residue is cautiously treated with cold water
  8. additionSaturated sodium bicarbonate is added
  9. extractionit is extracted with ethyl acetate (3×)
  10. extractionThe combined extract
  11. washis washed with brine
  12. customdried
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe residue is purified by chromatography
  16. washeluting with pentane-10 to 100% ether

출처 및 근거

ORD 기록
ord-a60c00aa524246eb92f144e60a468ac9
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405300B2

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