5-chloro-N-methylpyridin-2-amine → 1,1-bis(phenylsulphonyl)-2-[N-(5-chloropyrid-2-yl)-N-methylamino]ethene

HRID 542893

Reaktionsgleichung

Reaktionsgleichung von HRID 542893
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.C(O[CH:13]=[C:14]([S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])[S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16])C>Cl.C1(C)C=CC=CC=1.N12CCCC1=NCCC2>[C:27]1([S:24]([C:14]([S:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[CH:13][N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)[CH3:9])(=[O:25])=[O:26])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

6

Edukt 2

HCID 38370245-chloro-N-methylpyridin-2-amineHCID 124009381,1-Bis(phenylsulphonyl)-2-ethoxyethene

Produkt 1

HCID 202074401,1-bis(phenylsulphonyl)-2-[N-(5-chloropyrid-2-yl)-N-methylamino]ethene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 5-chloro-2-(methylamino)pyridine (0.41 g), 2-ethoxy-1,1-bis(phenylsulphonyl)ethene and concentrated hydrochloric acid (1 drop) in toluene (20 ml) was heated at reflux for 4 hours and then the mixture was treated with 1,5-diazabicyclo[4.3.0]-non-5-ene (3 drops) and heated at reflux for 18 hours. The reaction mixture was cooled and concentrated in vacuo to give an oil which was triturated with ethanol to give a brown solid which was recrystallised from toluene to give 1,1-bis(phenylsulphonyl)-2-[N-(5-chloropyrid-2-yl)-N-methylamino]ethene (0.2 g), mp. 205°-206° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureheated
  4. temperatureat reflux for 18 hours
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. customwas triturated with ethanol
  9. customto give a brown solid which
  10. customwas recrystallised from toluene

Quellen und Nachweise

ORD-Eintrag
ord-b3a9fe616479454fa1f454e11bde5baa
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659727

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