Dimethyl Sulfoxide → 2-(2-Hydroxy-5-nitrobenzyl)-5-methoxy-1-(4-methoxybenzenesulphonyl)-1,2-dihydroindazol-3-one

HRID 567724

反応式

HRID 567724 の反応式
COC1C=CC(S([O:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)[NH:15][N:14]=2)(=O)=O)=CC=1.[H-].[Na+].[OH:26][C:27]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:28]=1[CH2:29]Cl.[OH2:38].C[S:40]([CH3:42])=[O:41]>>[OH:26][C:27]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:28]=1[CH2:29][N:14]1[C:13](=[O:12])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]1[S:40]([C:42]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:38])=[O:41]

参加物

6

反応物 5

HCID 679Dimethyl Sulfoxide2 回HCID 962WaterHCID 24758Sodium hydrideHCID 763052-(Chloromethyl)-4-nitrophenolHCID 154290475-methoxy-1H-indazol-3-yl 4-methoxybenzenesulphonate

生成物 1

HCID 98053852-(2-Hydroxy-5-nitrobenzyl)-5-methoxy-1-(4-methoxybenzenesulphonyl)-1,2-dihydroindazol-3-one

実験手順

5.01 g (15 mmol) of 5-methoxy-1H-indazol-3-yl 4-methoxybenzenesulphonate are dissolved in 70 ml of DMSO and treated in portions with 1.5 g (37.5 mmol) of sodium hydride (60 percent). After stirring for 2 hours, a solution of 2.81 g (15 mmol) of 2-hydroxy-5-nitrobenzyl chloride in 25 ml of DMSO is added dropwise and the mixture is stirred at 90-100° C. for 3 hours. After cooling, 400 ml of water are added, and the mixture is stirred for 3 hours and extracted three times with 400 ml of ethyl acetate. The combined organic phases are washed with 100 ml of water, dried over sodium sulphate, distilled to dryness in vacuo and the residue is recrystallized from ethanol.

後処理

  1. stirringthe mixture is stirred at 90-100° C. for 3 hours
  2. temperatureAfter cooling
  3. stirringthe mixture is stirred for 3 hours
  4. extractionextracted three times with 400 ml of ethyl acetate
  5. washThe combined organic phases are washed with 100 ml of water
  6. dry with materialdried over sodium sulphate
  7. distillationdistilled to dryness in vacuo
  8. customthe residue is recrystallized from ethanol

出典と根拠

ORDレコード
ord-c071f75f633949b28c254c8a60b8ebe9
出典データセット
uspto-grants-2001_01
特許番号
US06180637B2

関連ノート

読み込み中…