Sulfisoxazole → 4-(2,4-Dinitrophenylamino)-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide

HRID 1899691Notes

Reaction equation

HRID 1899691 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]2[O:29][N:28]=[C:27]([CH3:30])[C:26]=2[CH3:31])(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCCC1>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]2[O:29][N:28]=[C:27]([CH3:30])[C:26]=2[CH3:31])(=[O:23])=[O:22])=[CH:17][CH:16]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5344SulfisoxazoleHCID 6264DinitrofluorobenzeneHCID 8471Triethylamine

Product 1

HCID 233728824-(2,4-Dinitrophenylamino)-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dinitrofluorobenzene (0.457 ml, 3.6 mmol) and 4-amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide (818 mg, 3.0 mmol) were dissolved in dry tetrahydrofuran (25 ml) and triethylamine (1.0 ml, 7.5 mmol) was added slowly. The reaction was stirred at room temperature for 48 h. The solvent and volatiles were removed under reduced pressure and the residue was partitioned between 1N HCl and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated and the residue was recrystallized from methanol to give 1.1 g (85%) yellow solid, m.p. 187° C.

Workup

  1. customThe solvent and volatiles were removed under reduced pressure
  2. customthe residue was partitioned between 1N HCl and ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-163aef0e06c446debc91a4439ec0c788
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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