Benzenesulfonamide → HCID 54389565, compound

HRID 727754Notes

Reaction equation

HRID 727754 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C:9]1([S:15]([NH2:18])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[N:18][S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])[CH:2]=1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 103713-PyridinecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 54389565HCID 54389565, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A stirred mixture consisting of 4.00 g (37 mmol) of 3-pyridinecarboxaldehyde, 5.88 g (37 mmol) of benzenesulfonamide and 20 mg of p-toluenesulfonic acid monohydrate in 120 mL of toluene was heated to reflux under a blanket of nitrogen. The reaction vessel was equipped with a Soxhlet extractor containing 4A molecular sieves. After heating 18 hours, the mixture was allowed to cool to approximately 40° C. and was filtered to remove colored impurities. Addition of hexane to the filtrate led to precipitation of a white solid. Filtration provided 9.10 g (73%) of sulfonimine: mp 123° C.; IR (Nujol) 1640, 1605, 1585, 1560, 1300, 1280, 1220, 860 cm-1 ; 1H NMR (CDCl3, TMS, 60 MHz) δ9.15 (s, 1), 8.9-8.7 (m, 2), 8.4-7.4 (m, 7).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a blanket of nitrogen
  3. customThe reaction vessel was equipped with a Soxhlet extractor
  4. temperatureAfter heating 18 hours
  5. filtrationwas filtered
  6. customto remove colored impurities
  7. additionAddition of hexane to the filtrate
  8. customled to precipitation of a white solid
  9. filtrationFiltration
  10. customprovided 9.10 g (73%) of sulfonimine

Sources & evidence

ORD record
ord-b7a91bffec724dcea20e83f712541263
Source dataset
uspto-grants-1991_09
Patent number
US05045223

Reaction notes

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