Benzenesulfonamide → N-Tricyclo[8.2.1.03,8]trideca-3(8),4.6-trien-13-ylidene-benzenesulfonamide

HRID 902437Notes

Reaction equation

HRID 902437 reaction equation
[CH:1]12[C:13](=O)[CH:10]([CH2:11][CH2:12]1)[CH2:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:2]2.[C:15]1([S:21]([NH2:24])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[CH:1]12[C:13](=[N:24][S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:23])=[O:22])[CH:10]([CH2:11][CH2:12]1)[CH2:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:2]2

Participants

4

Reactant 2

HCID 7370BenzenesulfonamideHCID 5260406Tricyclo[8.2.1.03,8]trideca-3,5,7-trien-13-one

Product 1

HCID 69301074N-Tricyclo[8.2.1.03,8]trideca-3(8),4.6-trien-13-ylidene-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-one (130 mg, 0.70 mmol) and benzenesulfonamide (110 mg, 0.70 mmol) were mixed in toluene (6 mL). Amberlyst-15 ion exchange resin (35 mg) was added, and the mixture was heated at reflux under Dean Stark conditions for 36 h. The mixture was concentrated and the crude sulfonylimine was used directly in the next step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under Dean Stark conditions for 36 h
  3. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-df9af48c530149dab87bd57b5e9ec178
Source dataset
uspto-grants-2008_04
Patent number
US07365196B2

Reaction notes

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