Sulfisoxazole → 4-[N'-(Ethoxycarbonylmethyl)ureido]-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide

HRID 1899689Notes

Reaction equation

HRID 1899689 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[O:16][N:15]=[C:14]([CH3:17])[C:13]=2[CH3:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]=[O:21]>CN(C)C=O>[CH2:26]([O:25][C:23]([CH2:22][NH:19][C:20](=[O:21])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[O:16][N:15]=[C:14]([CH3:17])[C:13]=2[CH3:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1)=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 5344SulfisoxazoleHCID 76283Ethyl isocyanatoacetate

Product 1

HCID 702095124-[N'-(Ethoxycarbonylmethyl)ureido]-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamideYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide (545 mg, 2.0 mmol) was dissolved in dry dimethylformamide (10 ml). Ethyl isocyanatoacetate (463 ml, 4.0 mmol) was added. The reaction was stirred at room temperature for 3 h and then heated at 80° C. for an additional 8 h. Dimethylformamide was removed under reduced pressure and the residue was recrystallized from acetonitrile/water to give 807 mg (90% yield) brownish solid, m.p. 115°-125° C.

Workup

  1. temperatureheated at 80° C. for an additional 8 h
  2. customDimethylformamide was removed under reduced pressure
  3. customthe residue was recrystallized from acetonitrile/water

Sources & evidence

ORD record
ord-498d8750c5104c12b8d10e77ef2b0769
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

Loading…