Ammonia → P-Toluenesulfonamide

HRID 1586190Notes

Reaction equation

HRID 1586190 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH3:12]>ClCCl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH2:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 6269P-ToluenesulfonamideYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution containing 4-toluenesulfonyl chloride (10 g, 52.45 mmol) in dichloromethane (100 mL) at -78° C., liquid ammonia (20 mL) was added. After the mixture was stirred at -78° C. for 4 h, precipitates were removed by filtration and the filtrate was concentrated in vacuo to remove the solvent. The residue was then recrystallized from n-hexane/ethyl acetate (v/v=2:5) to give 7.77 g (85.7%) of 4-toluenesulfonamide.

Workup

  1. customprecipitates
  2. customwere removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto remove the solvent
  5. customThe residue was then recrystallized from n-hexane/ethyl acetate (v/v=2:5)

Sources & evidence

ORD record
ord-d7300cbc36fe4278ab951ed138363adf
Source dataset
uspto-grants-1999_08
Patent number
US05942546

Reaction notes

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