Ethylene Glycol → HCID 22013108, compound

HRID 366006Notes

Reaction equation

HRID 366006 reaction equation
[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

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 18373415HCID 18373415, compound

Product 1

HCID 22013108HCID 22013108, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a418d522b8ad474f98b7fc405f0faeca
Source dataset
uspto-grants-2000_10
Patent number
US06127544

Reaction notes

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