P-Toluenesulfonamide → HCID 11052497, compound

HRID 640675Notes

Reaction equation

HRID 640675 reaction equation
[O-]CC.[Na+:4].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1>C(O)C>[Na+:4].[C:5]1([CH3:15])[CH:6]=[CH:7][C:8]([S:11]([NH-:14])(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6269P-ToluenesulfonamideHCID 2723922Sodium ethoxide

Product 1

HCID 11052497HCID 11052497, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of sodium ethoxide (23.8 g) in ethanol (anhydrous, 400 ml) is added toluene-4-sulfonamide (60 g) around 50 C. The formed slurry is heated up to reflux for 2 hours and then cooled to 20° C. The precipitated solid is collected by filtration, rinsed with anhydrous ethanol and dried under vacuum with nitrogen flow to give toluene-4-sulfonamide monosodium salt (61.3 g, yield: 90.6%).

Workup

  1. temperatureThe formed slurry is heated up
  2. temperatureto reflux for 2 hours
  3. filtrationThe precipitated solid is collected by filtration
  4. washrinsed with anhydrous ethanol
  5. customdried under vacuum with nitrogen flow

Sources & evidence

ORD record
ord-15a54049c27446a0a80db2845bf07ef2
Source dataset
uspto-grants-2010_04
Patent number
US07692015B2

Reaction notes

Loading…