Ethylene Glycol → HCID 22013108、化合物

HRID 366006ノート

反応式

HRID 366006 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-a418d522b8ad474f98b7fc405f0faeca
出典データセット
uspto-grants-2000_10
特許番号
US06127544

反応ノート

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