3-Nitrobenzenesulfonyl chloride → HCID 2885772, compound

HRID 1603768Notes

Reaction equation

HRID 1603768 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[N+:8]([C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9]>N1C=CC=CC=1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:17]([C:13]2[CH:12]=[C:11]([N+:8]([O-:10])=[O:9])[CH:16]=[CH:15][CH:14]=2)(=[O:18])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 100093-Aminopyridine

Product 1

HCID 2885772HCID 2885772, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-aminopyridine (2 g, 21.3 mmol) in pyridine (100 ml) was added 3-nitrobenzene sulphonyl chloride (4.43 g, 20 mmol) and the mixture was heated to 50° C. for 3 hours. After cooling it was partitioned between ethyl acetate and water and the organic washed with water (×2) and half saturated aqueous sodium chloride solution, separated, dried and evaporated to give a crude yield of 4.96 g. It was then triturated with dichloromethane and sonicated for 0.25 hours before being filtered and dried to give the product as a pink solid (4.279 g, 72%)

Workup

  1. temperatureAfter cooling it
  2. customwas partitioned between ethyl acetate and water
  3. washthe organic washed with water (×2) and half saturated aqueous sodium chloride solution
  4. customseparated
  5. customdried
  6. customevaporated
  7. customto give a crude yield of 4.96 g
  8. customIt was then triturated with dichloromethane
  9. customsonicated for 0.25 hours
  10. filtrationbefore being filtered
  11. customdried

Sources & evidence

ORD record
ord-4b7de3bd0d984e2ca564822ccfcc58b8
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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