Water → 2,5-Bis[4-(3,4-dimethyl-5-isoxazolyl)sulfamoylanilino]terephthalic acid

HRID 1291939

Reaction equation

HRID 1291939 reaction equation
C1(=O)[O:12][C:10](=[O:11])[CH:9]([CH3:13])[CH:8]([CH3:14])C(=O)OC(=O)CC1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[O:32][N:31]=[C:30]([CH3:33])[C:29]=2[CH3:34])(=[O:26])=[O:25])=[CH:20][CH:19]=1.[S:35](=[O:39])(=O)(O)[OH:36].[N+:40]([C:43]1[CH:44]=[C:45](S([O-])(=O)=O)[CH:46]=[CH:47][CH:48]=1)([O-])=O.[Na+].[OH-:54].[K+].[OH2:56]>CO>[CH3:33][C:30]1[C:29]([CH3:34])=[C:28]([NH:27][S:24]([C:21]2[CH:22]=[CH:23][C:18]([NH:17][C:14]3[CH:8]=[C:9]([C:10]([OH:12])=[O:11])[C:13]([NH:40][C:43]4[CH:44]=[CH:45][C:46]([S:35](=[O:39])(=[O:36])[NH:27][C:28]5[O:32][N:31]=[C:30]([CH3:33])[C:29]=5[CH3:34])=[CH:47][CH:48]=4)=[CH:19][C:18]=3[C:23]([OH:56])=[O:54])=[CH:19][CH:20]=2)(=[O:26])=[O:25])[O:32][N:31]=1

Participants

8

Reactant 6

HCID 962Water2×HCID 1118Sulfuric Acid2×HCID 5344SulfisoxazoleHCID 14797Potassium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 131720661Dimethylsuccinyl succinate

Product 1

HCID 189137082,5-Bis[4-(3,4-dimethyl-5-isoxazolyl)sulfamoylanilino]terephthalic acidYield 70.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To 150 g of methanol was added with stirring 20 g (87.6 mmol) of dimethylsuccinyl succinate, 53.9 g (201.6 mmol) of 4-amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide (Aldrich Chemical Co.), and 0.7 g of concentrated sulfuric acid. The reaction mixture was heated slowly to 95° to 97° C. and maintained at that temperature for five hours. After the reaction mixture was cooled to 50° C., 26 g of sodium 3-nitrobenzenesulfonate, 2 g of water, and 75 g of 45% aqueous potassium hydroxide were slowly added with stirring. The resultant mixture was then slowly heated to 90° C and maintained at that temperature for four hours. The reaction mixture was cooled to room temperature and added to 500 ml of water. Concentrated sulfuric acid was slowly added to produce a solid that was collected by filtration and washed with water. The wet presscake was dried in an oven to give 43 g (70.4% of theory) of 2,5-bis[4-(3,4-dimethyl-5-isoxazolyl)sulfamoylanilino]terephthalic acid.

Workup

  1. temperatureThe reaction mixture was heated slowly to 95° to 97° C.
  2. temperaturemaintained at that temperature for five hours
  3. temperaturemaintained at that temperature for four hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customto produce a solid
  6. filtrationthat was collected by filtration
  7. washwashed with water
  8. customThe wet presscake was dried in an oven

Sources & evidence

ORD record
ord-5bf4fed710744353ab0975c0e0ea28b7
Source dataset
uspto-grants-1998_05
Patent number
US05755873

Linked notes

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