Pyridine → N-[4-(4-methylphenoxy)phenyl]methanesulfonamide

HRID 1716292Notes

Reaction equation

HRID 1716292 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(Cl)Cl.O>C(Cl)Cl>[C:1]1([CH3:15])[CH:2]=[CH:3][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:10][CH:9]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 945194-(p-Tolyloxy)anilineHCID 21908982Water methylene chloride

Product 1

HCID 3858049N-[4-(4-methylphenoxy)phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-p-tolyloxy-phenylamine (0.87 g, 4.38 mmol) and pyridine (0.52 mL, 6.53 mmol) in dried CH2Cl2 (10 mL) under N2 at 0° C. was added methanesulfonyl chloride (0.41 mL, 5.26 mmol) dropwise. The mixture was stirred at 0° C. for 1 h and was then poured into CH2Cl2/H2O (10 mL/10 mL). The organic layer was washed with 2N HCl (aq) (3 mL), H2O, brine, dried (Na2SO4), and filtered through Celite. After removal of solvent, the crude product was purified by chromatography (silica gel, 45% EtOAc/hexanes) to give the titled compound. MS (EI) 278 (M+H)+.

Workup

  1. washThe organic layer was washed with 2N HCl (aq) (3 mL), H2O, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered through Celite
  4. customAfter removal of solvent
  5. customthe crude product was purified by chromatography (silica gel, 45% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a9842a4636e241bd8119ba316c86b4e1
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

Loading…