Ethylene Glycol → HCID 20492181, compound

HRID 434780Notes

Reaction equation

HRID 434780 reaction equation
[CH:1]([C:3]1[O:7][C:6]([CH2:8][S:9][CH2:10][CH2:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:5][CH:4]=1)=[O:2].[CH2:23](O)[CH2:24][OH:25]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:2]1[CH2:23][CH2:24][O:25][CH:1]1[C:3]1[O:7][C:6]([CH2:8][S:9][CH2:10][CH2:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 20492177HCID 20492177, compound

Product 1

HCID 20492181HCID 20492181, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A mixture of N-[2-[(5-formyl-2-furanylmethyl)thio]ethyl ]-1H-isoindole-1,3-(2H)-dione (15 g), p-toluenesulphonic acid (0.12 g) and 1,2-ethanediol (6.2 g) in benzene (160 ml) was refluxed under Dean-Starke conditions. After 6 hours, the solution was washed with a solution of sodium carbonate (1.2 g) in water (25 ml), dried (Na2CO3), decolourised (charcoal) and evaporated in vacuo. The semi-solid residue was suspended in ether (200 ml) and filtered off to give the title compound (13.5 g), m.p. 83°-85°.

Workup

  1. temperaturewas refluxed under Dean-Starke conditions
  2. washthe solution was washed with a solution of sodium carbonate (1.2 g) in water (25 ml)
  3. dry with materialdried (Na2CO3)
  4. customevaporated in vacuo
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-4e9159b5e1b94ddab7f1fa6756d30535
Source dataset
uspto-grants-1983_08
Patent number
US04399294

Reaction notes

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