Hydrochloric Acid → 3,5-Dichloro-2-(nitromethyl)pyridine

HRID 56041

반응식

HRID 56041 반응식
CC(C)([O-])C.[K+].[N+:7]([CH3:10])([O-:9])=[O:8].Cl[C:12]1[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][N:13]=1.Cl>CS(C)=O>[Cl:18][C:17]1[C:12]([CH2:10][N+:7]([O-:9])=[O:8])=[N:13][CH:14]=[C:15]([Cl:19])[CH:16]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 27666Pyridine, 2,3,5-trichloro-HCID 23665647Potassium tert-butoxide

생성물 1

HCID 1180714853,5-Dichloro-2-(nitromethyl)pyridine수율 35.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To 30.74 g of potassium tert-butoxide in 100 ml of dimethylsulfoxide, 16.72 g of nitromethane was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at room temperature for another 1 hour. Then, the reaction mixture was cooled with ice again, and to the reaction mixture, 25.00 g of 2,3,5-trichloropyridine in 100 ml of dimethylsulfoxide was added dropwise with stirring, and after the addition, the mixture was stirred at 70° C. for another 6 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, poured into 200 ml of 10% aqueous hydrochloric acid with stirring under cooling with ice and extracted with ethyl acetate (200 ml×1). The resulting organic layer was washed with water (100 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 5:95 to 10:90) as the eluent to obtain 10.10 g of the desired product as a pale yellow oil.

후처리

  1. temperatureunder cooling with ice
  2. additionafter the addition
  3. stirringthe mixture was stirred at room temperature for another 1 hour
  4. temperatureThen, the reaction mixture was cooled with ice again
  5. stirringwith stirring
  6. additionafter the addition
  7. stirringthe mixture was stirred at 70° C. for another 6 hours
  8. customAfter completion of the reaction
  9. stirringwith stirring
  10. temperatureunder cooling with ice
  11. extractionextracted with ethyl acetate (200 ml×1)
  12. washThe resulting organic layer was washed with water (100 ml×1)
  13. dry with materialdried over saturated aqueous sodium chloride
  14. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  15. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d6bb09296a55462fb5f3dd9738621fc4
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434684B2

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