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

HRID 2352000
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2352000
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
3×

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1575120c78c64fb18b58711871ec6d06
Quelldatensatz
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04874775

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