Potassium Carbonate → N-Phenyl-N-[(pyridin-3-yl)methyl]methanesulfonamide

HRID 2352000

반응식

HRID 2352000 반응식
[C:1]1([NH:7][CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]1([N:7]([CH2:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[S:22]([CH3:21])(=[O:24])=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 1082702N-(pyridin-3-ylmethyl)aniline

생성물 1

HCID 14720341N-Phenyl-N-[(pyridin-3-yl)methyl]methanesulfonamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A 3.7 g. portion of 3-(phenylaminomethyl)pyridine was dissolved in 20 ml. of dichloromethane, and to it was added 4.1 g. of potassium carbonate and 2.5 ml. of methanesulfonyl chloride. The mixture was stirred under reflux overnight, and was then diluted with 20 ml. of aqueous sodium bicarbonate and 20 ml. of dichloromethane. The organic phase was separated, washed with 20 ml. of water, dried over magnesium sulfate and evaporated under vacuum. The residue was triturated with diethyl ether and dried to give 4.9 g. of impure product. It was dissolved in 10 ml. of dichloromethane and 20 ml. of ethyl acetate and filtered. The filtrate was evaporated under vacuum, and the residue was triturated with petroleum ether, filtered and dried to obtain 4.4 g. of the desired product, m.p. 104°-105°.

후처리

  1. temperatureunder reflux overnight
  2. additionwas then diluted with 20 ml
  3. customThe organic phase was separated
  4. washwashed with 20 ml
  5. dry with materialof water, dried over magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue was triturated with diethyl ether
  8. customdried
  9. customto give 4.9 g
  10. dissolutionIt was dissolved in 10 ml
  11. filtrationof ethyl acetate and filtered
  12. customThe filtrate was evaporated under vacuum
  13. customthe residue was triturated with petroleum ether
  14. filtrationfiltered
  15. customdried
  16. customto obtain 4.4 g

출처 및 근거

ORD 기록
ord-1575120c78c64fb18b58711871ec6d06
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04874775

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