Sodium Chloride → N-[4-(4-methoxyphenyl)phenyl]methanesulfonamide

HRID 1883700Notes

Reaction equation

HRID 1883700 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>C(O)C.C1(C)C=CC=CC=1>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 706841N-(4-Bromophenyl)methanesulfonamide

Product 1

HCID 23508422N-[4-(4-methoxyphenyl)phenyl]methanesulfonamideYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture composed of 500 mg of N-(4-bromophenyl)methane-sulfonamide, 334 mg of 4-methoxyphenyl boronic acid, 55.5 mg of tetrakis-triphenylphosphinepalladium, 2 ml of a 2 M aqueous solution of sodium carbonate, 4 ml of toluene, and 1 ml of ethanol was heated under. reflux for 5 hours in an atmosphere of nitrogen. After the reaction mixture was poured into a saturated aqueous solution of sodium chloride, the product was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the resulting crude product was purified by silica gel column chromatography (using a 7:1 mixture of chloroform and tetrahydrofuran as the eluent) to obtain 94 mg of N-(4′-methoxybiphenyl-4-yl)methanesulfonamide.

Workup

  1. temperaturewas heated under
  2. temperaturereflux for 5 hours in an atmosphere of nitrogen
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe resulting crude product was purified by silica gel column chromatography (
  8. additiona 7:1 mixture of chloroform and tetrahydrofuran as the eluent)

Sources & evidence

ORD record
ord-b0c597f2972d4de0a45dac2440223af3
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

Loading…