Methyl iodide → N-tert-butyl-6-chloro-N-methylpyridine-3-sulfonamide

HRID 2199591Notes

Reaction equation

HRID 2199591 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:10]=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[C:18]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]([N:5]([CH3:18])[S:6]([C:9]1[CH:10]=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)(=[O:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 4729821N-tert-butyl-6-chloropyridine-3-sulfonamide

Product 1

HCID 86659955N-tert-butyl-6-chloro-N-methylpyridine-3-sulfonamideYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.97 g (3.9 mmol) of N-tert-butyl-6-chloropyridine-3-sulfonamide, 2.43 mL (39 mmol) of methyl iodide and 5.4 g (39 mmol) of K2CO3 in 40 mL of acetone is refluxed for 12 hours. The reaction medium is filtered at room temperature, and the filtrate is concentrated under reduced pressure. The residue obtained is purified on silica gel, eluting with a cyclohexane/EtOAc gradient of from 0 to 20% EtOAc, to give 0.66 g of N-tert-butyl-6-chloro-N-methylpyridine-3-sulfonamide in the form of a yellow solid.

Workup

  1. temperatureis refluxed for 12 hours
  2. filtrationThe reaction medium is filtered at room temperature
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified on silica gel
  6. washeluting with a cyclohexane/EtOAc gradient of from 0 to 20% EtOAc

Sources & evidence

ORD record
ord-b0fc3b730f7f45ea8d223215aa52e3a7
Source dataset
uspto-grants-2016_06
Patent number
US09359329B2

Reaction notes

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