Ethylene Glycol → HCID 22013108、化合物

HRID 618553ノート

反応式

HRID 618553 の反応式
[CH:1]([CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)=[O:26])([NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[O:15])[C:5]1=[O:35])=[O:2].[CH2:36](O)[CH2:37][OH:38].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:34][C:31]1[CH:30]=[CH:29][C:28]([NH:27][C:25]([CH2:24][C:6]2([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[O:15])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH2:3][CH:1]3[O:38][CH2:37][CH2:36][O:2]3)[C:5]2=[O:35])=[O:26])=[CH:33][CH:32]=1

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 18373415HCID 18373415、化合物

生成物 1

HCID 22013108HCID 22013108、化合物収率 68%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 0.294 g of (RS)-1-(formylmethyl)-3-((4-methylphenyl)aminocarbonylmethyl)-3-(N'-(4-methylphenyl)ureido)indolin-2-one in 50 ml of toluene were added 0.5 ml of ethylene glycol and 10 mg of p-toluenesulfonic acid. The mixture was heated under reflux for 6 hours while azeotropically removing produced water together with toluene. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give 0.220 g (68%) of the title compound.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customwhile azeotropically removing
  4. customproduced water together with toluene
  5. washThe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-24bb65fe448f48639caccf94b205db70
出典データセット
uspto-grants-1999_09
特許番号
US05952511

反応ノート

読み込み中…