4-Methoxybenzenesulfonyl chloride → HCID 15435816, compound

HRID 1741015Notes

Reaction equation

HRID 1741015 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:15][C:10]2[C:9](/[CH:8]=[CH:7]/[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 14590315HCID 14590315, compound

Product 1

HCID 15435816HCID 15435816, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 10 ml of pyridine was dissolved 0.8 g of the (E)-3-(2-phenylethenyl)-2-aminopyridine obtained in Reference Example 1. To this solution was added 0.92 g of p-methoxyphenylsulfonyl chloride gradually under ice-cooling and the mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was evaporated off and the resulting residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=9/1). The crystal crop thus obtained was recrystallized from ethanol to provide 0.77 g of the desired compound (yellow plates). m.p. 152-155° C. Elemental analysis for C20H19N2O3S

Workup

  1. customobtained in Reference Example 1
  2. temperaturecooling
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated off
  5. customthe resulting residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=9/1)
  6. customThe crystal crop thus obtained
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-e5284ce257e747808bf73d8be3bc9dc0
Source dataset
uspto-grants-1999_10
Patent number
US05972976

Reaction notes

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