Methyl iodide → 4-bromo-N-(3-methoxyphenyl)-N-methylbenzenesulfonamide

HRID 2046074Notes

Reaction equation

HRID 2046074 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+].CI>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

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 33610674-bromo-N-(3-methoxyphenyl)benzenesulfonamide

Product 1

HCID 620032844-bromo-N-(3-methoxyphenyl)-N-methylbenzenesulfonamideYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of the product of Step A (0.5 g 1.46 mmol) and K2CO3 (0.5 g) in anhydrous DMF (7 ml) was added CH3I (1 ml) and the stirring continued for 0.5 h at 50° C. The mixture was diluted to 50 ml with H2O and extracted with EtOAc (50 ml). The organic layer was washed with H2O and dried over MgSO4, passed through silica gel bead and the filtrate was evaporated to dryness to give the title compound (0.5 g, 96%) as pale solid. 1H-NMR (CDCl3) 7.58 (d, 2H, J=8.64 Hz); 7.40 (d, 2H, J=8.67 Hz); 7.18 (t, 1H, J=8.15 Hz); 6.80 (dd, 1H, J=8.34, 2.5 Hz); 6.69 (t, 1H, J=2.20 Hz); 6.58 (bd, 1H); 3.75 (s, 3H, OMe); 3.14 (s, 3H, N-Me).

Workup

  1. extractionextracted with EtOAc (50 ml)
  2. washThe organic layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-c1e99e135f37409ba28295f780415aa8
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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