Water → HCID 90332514, compound

HRID 595692Notes

Reaction equation

HRID 595692 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N:15]([CH3:20])[S:16]([CH3:19])(=[O:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59233662N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide

Product 1

HCID 90332514HCID 90332514, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide (30 g, 0.11 mol) and K2CO3 (14.9 g, 0.11 mol) in DMF (300 mL) was added dropwise CH3I (15.3 g, 0.11 mol) at 0° C. under N2, and then the mixture was stirred for 1 hour at this temperature. H2O was added to the mixture and extracted with dichloromethane. The combined organic layer was washed with H2O, brine, dried over Na2SO4, filtrated and concentrated in vacuo to give N-(4-(benzyloxy)pyridin-3-yl)-N-methylmethanesulfonamide (15 g, yield: 50%), which was used for the next step without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.46 (s, 1H), 8.41 (d, J=6.0 Hz, 1H), 7.37˜7.39 (m, 5H), 6.94 (d, J=6.0 Hz, 1H), 5.15 (s, 2H), 3.22 (s, 3H), 2.79 (s, 3H). MS (M+H)+: 293.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layer was washed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e059e11d9274725a50364198d7df709
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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