Hydrochloric Acid → 2-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid

HRID 1464174ノート

反応式

HRID 1464174 の反応式
C([O:4][C:5]1[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:14][C:6]=1[C:7]([O:9]CC(C)C)=[O:8])(=O)C.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH2:36].S(=O)(=O)(O)O.[OH-].[K+].Cl>ClCCl.C(O)C>[OH:4][C:5]1[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:36][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:14][C:6]=1[C:7]([OH:9])=[O:8]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 104392-AminopyridineHCID 14797Potassium HydroxideHCID 53789228Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate

生成物 1

HCID 543430162-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate (1.99 g, 0.0046 mol) and 2-pyridinamine (1.3 g, 0.0138 mol) was stirred in dichloromethane (10 ml) at 45° C. for 1 h. After cooling to room temperature dichloromethane (20 ml) and 2M sulfuric acid (20 ml) were added. The precipitated solid (1.3 g) was collected and washed with water. The organic phase was taken to dryness and the residue treated with boiling methanol containing ammonia (2 ml) for 20 min. After cooling, 0.6 g was collected which was combined with the first crop. The combined material (1.9 g) was refluxed with potassium hydroxide (1 g) in water (50 ml). After acidification and filtration, the solid residue was dissolved in 70% ethanol with about 3 equivalents of potassium hydroxide at the boiling point and acidified while boiling with hydrochloric acid. After filtration and drying, the yield was 1.25 g (70%).

後処理

  1. additionwere added
  2. customThe precipitated solid (1.3 g) was collected
  3. washwashed with water
  4. additionthe residue treated with boiling methanol
  5. additioncontaining ammonia (2 ml) for 20 min
  6. temperatureAfter cooling
  7. custom0.6 g was collected which
  8. temperatureThe combined material (1.9 g) was refluxed with potassium hydroxide (1 g) in water (50 ml)
  9. filtrationAfter acidification and filtration
  10. filtrationAfter filtration
  11. customdrying

出典と根拠

ORDレコード
ord-234b4b41977243faaa958ff2b5483e50
出典データセット
uspto-grants-1994_04
特許番号
US05302718

反応ノート

読み込み中…