Sodium Bicarbonate → N-{4-[4-(4-Nitropyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide

HRID 2232404Notes

Reaction equation

HRID 2232404 reaction equation
Cl.[N:2]1([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][N:21]=1.C(=O)(O)[O-].[Na+]>C(O)CCC>[N+:26]([C:24]1[CH:23]=[CH:22][N:21]=[C:20]([N:5]2[CH2:6][CH2:7][N:2]([C:8]3[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:12][CH:13]=3)[CH2:3][CH2:4]2)[CH:25]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7351522-Chloro-4-nitropyridineHCID 18759927N-[4-(piperazin-1-yl)phenyl]methanesulfonamide hydrochloride

Product 1

HCID 21283530N-{4-[4-(4-Nitropyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of the product of (iii) above (1.46 g), 2-chloro-4-nitropyridine (0.79 g) and sodium bicarbonate (1.26 g) in n-butanol (30 ml) were heated under reflux with stirring for 24 hours and then cooled and filtered. The solid was washed with methanol and the combined filtrate and washings were evaporated to give a gum that was chromatographed on silica gel. Elution with dichloromethane, gradually increasing the polarity to dichloromethane/methanol (4:1) gave a mixture of the desired product, together with some N-{4-[4-(2-chloropyrid-4-yl)piperazin-1-yl]phenyl}methanesulphonamide biproduct, as a solid. The solid was crystallised four times from methanol to give pure N-{4-[4-(4-nitropyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide (0.36 g), m.p. 182°-183° C. Found: C,50.90; H,5.07; N,18.51. C16H19N5O4S requires: C,50.91; H,5.07; N,18.56%.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe solid was washed with methanol
  6. customthe combined filtrate and washings were evaporated
  7. customto give a gum that
  8. customwas chromatographed on silica gel
  9. washElution with dichloromethane
  10. temperaturegradually increasing the polarity to dichloromethane/methanol (4:1)
  11. customgave

Sources & evidence

ORD record
ord-1b3324e54c4e494ebe4ba925457e714b
Source dataset
uspto-grants-1988_11
Patent number
US04788196

Reaction notes

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