Sulfisoxazole → 4'-[(3,4-Dimethyl-5-isoxazolyl)sulfamoyl]succinanilic acid

HRID 1385847

反応式

HRID 1385847 の反応式
[CH3:1][C:2]1[C:3]([CH3:18])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)(=[O:10])=[O:9].[C:19]1(=[O:25])[O:24][C:22](=[O:23])[CH2:21][CH2:20]1>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:18][C:3]1[C:2]([CH3:1])=[C:6]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:19](=[O:25])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[O:5][N:4]=1

参加物

5

反応物 2

HCID 5344SulfisoxazoleHCID 7922Succinic anhydride

生成物 1

HCID 217159674'-[(3,4-Dimethyl-5-isoxazolyl)sulfamoyl]succinanilic acid収率 76.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of sulfisoxazole (267 mg, 1.00 mmol) in DMF (10 ml) was added succinic anhydride (1.00 g, 10.0 mmol) and 4-dimethylaminopyridine (122 mg, 1.00 mmol). The reaction mixture was stirred at 80° C. for 2 hours and then concentrated. The residue was taken up in 5% aqueous sodium bicarbonate solution and extracted with ethyl acetate. The aqueous solution was acidified with dilute hydrochloric acid and organic material was extracted into ethyl acetate. The organic phase was washed with dilute hydrochloric acid, water and brine, treated with active charcoal and dried (MgSO4). The solution was filtered and concentrated to give 280 mg (76%) of white solid. The structure was verified by 1H (300 MHz) and 13C (75 MHz) NMR spectroscopy. Further characterisation was carried out using MALDI mass spectrometry (ACH matrix), giving a M+Na peak at m/z 390 and a M+K peak at m/z 406 as expected.

後処理

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. extractionwas extracted into ethyl acetate
  4. washThe organic phase was washed with dilute hydrochloric acid, water and brine
  5. additiontreated with active charcoal
  6. dry with materialdried (MgSO4)
  7. filtrationThe solution was filtered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-4e5edefe1d0849a9a9dee0640ecccbc2
出典データセット
uspto-grants-2001_07
特許番号
US06264917B1

関連ノート

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