Sulfathiazole → HCID 86618115, compound

HRID 1696145Notes

Reaction equation

HRID 1696145 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([S:8]([NH:11][C:12]2[S:16][CH:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:2]=1.[C:17]1(=[O:23])O[C:20](=[O:21])[CH:19]=[CH:18]1>>[S:16]1[CH:15]=[CH:14][N:13]=[C:12]1[NH:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:1][CH:2]=1)(=[O:10])=[O:9].[NH:7]1[C:20](=[O:21])[CH:19]=[CH:18][C:17]1=[O:23]

Participants

3

Reactant 2

HCID 5340SulfathiazoleHCID 7923Maleic Anhydride

Product 1

HCID 86618115HCID 86618115, compoundYield 30.4%

Procedure

Prepared using general procedure 44. A mixture of sulfathiazole (5 gm, 19.5 mmol) and maleic anhydride (1.92 g, 19.5 mmol) was heated under refluxed for 16 hrs. The reaction was cooled to RT and then to 0° C. for 4 hrs. The formed precipitate was filtered off and washed with cold water. The crude solid was dissolved in CH2Cl2 and absorbed onto Celite. Purification via silica gel chromatography using 10% MeOH in CH2Cl2 gave (1H-pyrrole-2,5-dione)-N-(thiazol-2-yl)benzene sulfonamide (2 g, 30%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=336.2; tR=2.12 min.

Workup

  1. customPrepared
  2. temperaturewas heated
  3. temperatureunder refluxed for 16 hrs
  4. filtrationThe formed precipitate was filtered off
  5. washwashed with cold water
  6. dissolutionThe crude solid was dissolved in CH2Cl2
  7. customabsorbed onto Celite
  8. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-6bd58ac1a22246ffa4d810ef1fd6f631
Source dataset
uspto-grants-2012_04
Patent number
US08163720B2

Reaction notes

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