Water → HCID 86721868, compound

HRID 1049009Notes

Reaction equation

HRID 1049009 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH:27]([CH3:29])[CH3:28].O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:26][CH:27]([CH3:29])[CH3:28])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 5735404-Fluoro-N-(4-fluorophenyl)benzenesulfonamide

Product 1

HCID 86721868HCID 86721868, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-fluoro-N-(4-fluoro-phenyl)-benzenesulfonamide (1.0 g, 3.7 mmol) and K2CO3 (1.03 g, 7.4 mmol) in dimethylformamide (5 mL) was added 1-bromo-2-methylpropane (1.21 mL, 11.2 mmol). The mixture was heated at 100° C. in a microwave reactor for 3 hours. Water was added and then extracted with EtOAc, washed with brine, dried with Na2SO4 then concentrated. The crude product was re-dissolved in cyclohexane then concentrated to give 4-fluoro-N-(4-fluoro-phenyl)-N-isobutyl-benzenesulfonamide (1.05 g, 86%). 1H NMR (300 MHz, CDCl3): δ 7.56-7.57 (m, 2H), 7.12-7.13 (m, 2H), 7.00 (d, 4H), 3.28 (d, 2H), 1.54 (m, 1H), 0.91 (d, 6H).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. concentrationthen concentrated
  5. dissolutionThe crude product was re-dissolved in cyclohexane
  6. concentrationthen concentrated

Sources & evidence

ORD record
ord-10f7e50b87df4b9d8ba5bad77aa97339
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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