Dimethylmaleic anhydride → 2-chloro-5-(2,5-dihydro-3,4-dimethyl-2,5-dioxo-1H-pyrrol-1-yl)benzenesulfonamide

HRID 4901

Reaction equation

HRID 4901 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:7]=1.[CH3:13][C:14]1[C:15]([O:17][C:18](=O)[C:19]=1[CH3:20])=[O:16]>N1C=CC=CC=1>[Cl:12][C:5]1[CH:4]=[CH:3][C:2]([N:1]2[C:15](=[O:16])[C:14]([CH3:13])=[C:19]([CH3:20])[C:18]2=[O:17])=[CH:7][C:6]=1[S:8]([NH2:11])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 748345-Amino-2-chlorobenzenesulfonamide

Product 1

HCID 148372102-chloro-5-(2,5-dihydro-3,4-dimethyl-2,5-dioxo-1H-pyrrol-1-yl)benzenesulfonamideYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 3 ml of pyridine, 1 mmol of 5-amino-2-chlorobenzenesulfonamide and 1.05 mmol of 2,3-dimethylmaleic anhydride were stirred at 90-100° C. for 9 hours. Pyridine was then distilled off from the reaction mixture, followed by the addition of 20 ml of ice water and 0.1 ml of 35% hydrochloric acid to the solid residue. After the mixture thus formed was stirred for 20 minutes, the resulting precipitate was collected by filtration and then dried in air. Yield: 93%. Its physicochemical properties are shown in Table 8.

Workup

  1. distillationPyridine was then distilled off from the reaction mixture
  2. additionfollowed by the addition of 20 ml of ice water and 0.1 ml of 35% hydrochloric acid to the solid residue
  3. customAfter the mixture thus formed
  4. filtrationthe resulting precipitate was collected by filtration
  5. customdried in air

Sources & evidence

ORD record
ord-0486b163d93d4c4098549fecca2a4eab
Source dataset
uspto-grants-1993_09
Patent number
US05242894

Linked notes

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