Benzenesulfonamide → HCID 811309, compound

HRID 727753Notes

Reaction equation

HRID 727753 reaction equation
C[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[S:7])=[CH:4][CH:3]=1.[C:10]1([S:16]([NH2:19])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:21][S:7][C:6](=[N:19][S:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:18])=[O:17])[C:5]1[CH:4]=[CH:3][CH:2]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 521998p-Toluenesulfonic acid monohydrateHCID 181775354-Methylthiobenzaldehyde

Product 1

HCID 811309HCID 811309, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture consisting of 2.60 g (17.2 mmol) of 4-methylthiobenzaldehyde, 2.70 g (17.2 mmol) cf benzenesulfonamide and 20 mg of p-toluenesulfonic acid monohydrate in 150 mL of toluene was heated to reflux. The reaction vessel was equipped with a Soxhlet extractor containing 4A molecular sieves. After heating 8 hours, the mixture was allowed to cool to room temperature and was concentrated to afford 4.60 g (92%) of sulfonimine as light tan crystals: mp 1.50°-155° C.; 1H NMR (CDCl3, TMS ext std) δ9.15 (s, 1), 8.27-7.18 (m, 9), 2.53 (s, 3).

Workup

  1. temperaturewas heated to reflux
  2. customThe reaction vessel was equipped with a Soxhlet extractor
  3. temperatureAfter heating 8 hours
  4. concentrationwas concentrated
  5. customto afford 4.60 g (92%) of sulfonimine as light tan crystals

Sources & evidence

ORD record
ord-dfd7002ed6cc40d198aa08026b6446e8
Source dataset
uspto-grants-1991_09
Patent number
US05045223

Reaction notes

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