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

HRID 542893

Reaction equation

HRID 542893 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneCatalystHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b3a9fe616479454fa1f454e11bde5baa
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Linked notes

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