Cyclohexene → HCID 16786647, compound

HRID 2183755Notes

Reaction equation

HRID 2183755 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH2:13][CH2:14][NH:15]C(=O)OCC2C=CC=CC=2)(=[O:12])=[O:11])=[CH:5][CH:4]=1.C1CCCCC=1>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:15][CH2:14][CH2:13][S:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:12]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 22475452HCID 22475452, compound

Product 1

HCID 16786647HCID 16786647, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution comprised of benzyl 2-(4-methoxyphenylsulfamoyl)ethylcarbamate (2.78 g, 7.63 mmol), prepared as in Reference 1, in ethanol (20 mL) and cyclohexene (20 mL) was treated with 20% palladium hydroxide (0.95 g). The mixture was heated at reflux for 2 hours, cooled, and concentrated to dryness. The solid was triturated with ether, filtered and dried to provide 2-amino-N-(4-methoxyphenyl)ethanesulfonamide (1.08 grams, 61% yield). 1H NMR (DMSO-d6): 2.86 (2H, t, J=6.4 Hz); 3.04 (2H, t, J=6.4 Hz); 3.72 (3H, s); 4.16 (2H, br. s); 6.87 (2H, d, J=9 Hz); 7.05 (2H, d, J=9 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated to dryness
  5. customThe solid was triturated with ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-1d1239f5e02f4c309fda8007564951c3
Source dataset
uspto-grants-2005_05
Patent number
US06900237B2

Reaction notes

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