Ethyl Acetate → N-{4-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]phenyl}-N-methylmethanesulphonamide

HRID 256606Notes

Reaction equation

HRID 256606 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[SH:14][C:15]1[CH:16]=[C:17]([C:21]2([O:27][CH3:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.[Cu]Cl.O>[CH3:28][O:27][C:21]1([C:17]2[CH:16]=[C:15]([S:14][C:2]3[CH:7]=[CH:6][C:5]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=3)[CH:20]=[CH:19][CH:18]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 13920676N-(4-Iodophenyl)-N-methylmethanesulphonamideHCID 193757154-(3-Mercaptophenyl)-4-methoxytetrahydropyran

Product 1

HCID 19785586N-{4-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]phenyl}-N-methylmethanesulphonamide

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-iodophenyl)-N-methylmethanesulphonamide (0.31 g, 1 mmol), 4-(3-mercaptophenyl)-4-methoxytetrahydropyran (0.22 g), potassium carbonate (20 mg) and copper (I) chloride (30 mg) in DMF (20 ml) was heated to 140° C. and stirred for 3 hours. Ethyl acetate (40 ml) and water (40 ml) were added and the mixture was filtered through celite. The filtrate was washed with water (40 ml) and brine (40 ml), dried (MgSO4) and the solvent evaporated. The product was purified by column chromatography, thus N-{4-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]phenyl}-N-methylmethanesulphonamide was obtained as an oil (0.12 g, 42%). NMR Spectrum 1.85-2.10 (4H, m), 2.85 (3H, s) 3.00 (3H, s), 3.30 (3H, s), 3.75-3.90 (4H, m), 7.25-7.35 (8H, m).

Workup

  1. filtrationthe mixture was filtered through celite
  2. washThe filtrate was washed with water (40 ml) and brine (40 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated
  5. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-19103a9c9d644555b7ad090d95e37f36
Source dataset
uspto-grants-1993_11
Patent number
US05258399

Reaction notes

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