1,3-Cyclohexadiene → 4-(Aminomethyl)-N-methylbenzene-1-sulfonamide

HRID 2382935Notes

Reaction equation

HRID 2382935 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][CH3:15])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=[N+]=[N-].C1CCC=CC=1>CO.[OH-].[Pd+2].[OH-]>[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][CH3:15])(=[O:13])=[O:12])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 116051,3-CyclohexadieneHCID 596679814-azidomethyl-N-methyl-benzenesulfonamide

Product 1

HCID 164609784-(Aminomethyl)-N-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-azidomethyl-N-methyl-benzenesulfonamide (2.20 g, 10.0 mmol), cyclohexadiene (8.90 mL, 90.0 mmol) and palladium hydroxide (20% on carbon, 1.4 g, 2.0 mmol) in MeOH (20 mL) was warmed at 65° C. for 2 hours. The solution was cooled to room temperature and filtered through diatomaceous earth. The solvent was removed in vacuo to afford 4-aminomethyl-N-methyl-benzenesulfonamide.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1cbcb44ce13b4734af822844787912fb
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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