Ethyl Bromide → HCID 178464531, compound

HRID 2057235Notes

Reaction equation

HRID 2057235 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[CH3:29]>CN(C=O)C>[CH2:28]([N:8]([C@H:5]1[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH3:29]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 178527590HCID 178527590, compound

Product 1

HCID 178464531HCID 178464531, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

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).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in CH2Cl2
  3. customThe phases were separated
  4. extractionthe inorganic one was extracted CH2Cl2
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe crude product was purified by column chromatography on silica gel with CH2Cl2/MeOH 95:5

Sources & evidence

ORD record
ord-855f69f48b5f4f1f837aaaf20f0458ca
Source dataset
uspto-grants-2008_02
Patent number
US07335687B2

Reaction notes

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