Ethylene Glycol → HCID 44422726, compound

HRID 2209285Notes

Reaction equation

HRID 2209285 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH2:13](O)[CH2:14][OH:15].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([O:15][CH2:14][CH2:13][O:12]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 957161H-Indole-2,3-dione, 6-bromo-

Product 1

HCID 44422726HCID 44422726, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into the solution of 6-bromoindoline-2,3-dione (3.3 g) in Toluene (90 mL), was added Ethylene Glycol (9 g) and p-TsOH (555 mg). The reaction was heated to reflux and water was removed. After completion of the reaction, Toluene was removed, the residue was purified by silica gel column chromatography to provide 3.38 g of 6′-bromospiro[[1,3]dioxolane-2,3′-indolin]-2′-one. 1H NMR (400 MHz, Chloroform-d) δ 7.59 (br., 1H), 7.21 (d, J=1.1 Hz, 2H), 7.00 (s, 1H), 4.60-4.51 (m, 2H), 4.35-4.27 (m, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customwater was removed
  4. customAfter completion of the reaction, Toluene
  5. customwas removed
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ee1895421a584127a3a464ac9c9bd5ec
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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