Potassium Carbonate → 4-bromo-N-(3-methoxyphenyl)-N-methylbenzenesulfonamide

HRID 710336Notes

Reaction equation

HRID 710336 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:20]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH3:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 33610674-bromo-N-(3-methoxyphenyl)benzenesulfonamide

Product 1

HCID 620032844-bromo-N-(3-methoxyphenyl)-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4-bromo-N-(3-methoxyphenyl)benzenesulphonamide (0.5 g 1.46 mmol) and K2CO3 (0.5 g) in anhydrous DMF (7 ml) MeI (1 ml) was added and this was stirred at 50° C. for 0.5 h. The mixture was diluted to 50 ml with H2O and extracted in EtOAc (50 ml). The organic layer was washed with H2O, dried over MgSO4, filtered and the filtrate was passed through silica gel bead. The filtrate was evaporated to dryness to give the product (0.5 g; 96%), as a pale solid. 1H-NMR (CDCl3) 3.14 (5, 3H); 3.75 (s, 3H); 6.58 (broad d, 1H), 6.69 (t, 1H, J=2.20 Hz); 6.80 (dd, 1H, J=2.5, 8.34, Hz); 7.18 (tr, 1H, J=8.15 Hz); 7.40 (d, 2H, J=8.67 Hz); 7.58 (d, 2H, J=8.64 Hz).

Workup

  1. extractionextracted in EtOAc (50 ml)
  2. washThe organic layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customto give the product (0.5 g; 96%)

Sources & evidence

ORD record
ord-70dc8b915bbf4debb88057ea4877ba04
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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