Ammonia → Benzenesulfonamide, 2,5-dimethoxy-

HRID 1252337Notes

Reaction equation

HRID 1252337 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[S:11](Cl)(=[O:13])=[O:12].[NH3:15]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[S:11]([NH2:15])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 1370252,5-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 209044Benzenesulfonamide, 2,5-dimethoxy-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 15.0 g (0.063 mole) of 2,5-dimethoxybenzenesulfonyl chloride in 150 mL of tetrahydrofuran was added dropwise 80 mL of ammonia (28% aqueous solution). After complete addition the mixture was allowed to stir for 1.75 hours at room temperature. Upon standing the mixture separated into two phases. The organic phase was removed from the aqueous phase and was evaporated under reduced pressure to leave a solid residue. This residue was recrystallized from hot water (125 mL) and ethanol (40 mL) to yield 13.1 g of 2,5-dimethoxyphenylsulfonamide (mp 146.5-148.5).

Workup

  1. additionAfter complete addition the mixture
  2. customseparated into two phases
  3. customThe organic phase was removed from the aqueous phase
  4. customwas evaporated under reduced pressure
  5. customto leave a solid residue
  6. customThis residue was recrystallized from hot water (125 mL) and ethanol (40 mL)

Sources & evidence

ORD record
ord-9237d0d8d56e4e399868325df64a78a4
Source dataset
uspto-grants-1988_05
Patent number
US04743291

Reaction notes

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