Reaction #53837

ord-1d8749fc54a14e59a78f3c8bf8bfed5d

Reaction equation

O=S(=O)(N[C@H]1CC[C@H](O)CC1)c1ccc(C(F)(F)F)cc1
trans-N-(4-Hydroxy-cyclohexyl)-4-trifluoromethyl-benzenesulfonamide
O=C([O-])[O-].[K+].[K+]
K2CO3
CCBr
ethyl bromide
→
CCN([C@H]1CC[C@H](O)CC1)S(=O)(=O)c1ccc(C(F)(F)F)cc1
trans-N-Ethyl-N-(4-hydroxy-cyclohexyl)-4-trifluoromethyl-benzenesulfonamide
Yield 38.0%

Reactants

O=S(=O)(N[C@H]1CC[C@H](O)CC1)c1ccc(C(F)(F)F)cc1
trans-N-(4-Hydroxy-cyclohexyl)-4-trifluoromethyl-benzenesulfonamide
O=C([O-])[O-].[K+].[K+]
K2CO3
CCBr
ethyl bromide

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Temperature
35°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated in vacuo
  2. 2
    workup.DISSOLUTIONdissolved in CH2Cl2
  3. 3
    OtherThe phases were separated
  4. 4
    Extractionthe inorganic one was extracted CH2Cl2
  5. 5
    Washthe combined organic phases were washed with brine
  6. 6
    Dryingdried over Na2SO4
  7. 7
    OtherThe crude product was purified by column chromatography on silica gel with CH2Cl2/MeOH 95:5

Procedure

To 4 g (12.4 mmol) trans-N-(4-Hydroxy-cyclohexyl)-4-trifluoromethyl-benzenesulfonamide in 20 ml DMF were added 5.1 g (37.1 mmol, 3.3 eq) K2CO3 and 2.04 ml (27.2 mmol, 2.2 eq) ethyl bromide. The mixture was stirred at 35° C. over night, concentrated in vacuo and dissolved in CH2Cl2 and water. The phases were separated and the inorganic one was extracted CH2Cl2, the combined organic phases were washed with brine and dried over Na2SO4. The crude product was purified by column chromatography on silica gel with CH2Cl2/MeOH 95:5 to yield 1.6 g (38%) trans-N-Ethyl-N-(4-hydroxy-cyclohexyl)-4-trifluoromethyl-benzenesulfonamide as brown oil, MS: 351(M).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858651B2uspto-grants-2005_02