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

HRID 1291939

반응식

HRID 1291939 반응식
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

참가 물질

8

반응물 6

HCID 962Water2회HCID 1118Sulfuric Acid2회HCID 5344SulfisoxazoleHCID 14797Potassium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 131720661Dimethylsuccinyl succinate

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5bf4fed710744353ab0975c0e0ea28b7
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05755873

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