Ethylene Glycol → Ethylene glycol bismaleurate

HRID 1858060Notes

Reaction equation

HRID 1858060 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]([N:8]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]1=[O:14])(=[O:7])[NH2:6]>C(#N)C.[Cl-].[Zn+2].[Cl-]>[C:12]([O:3][CH2:2][CH2:1][O:4][C:12](=[O:13])/[CH:11]=[CH:10]\[C:9](=[O:14])[NH:8][C:5](=[O:7])[NH2:6])(=[O:13])/[CH:11]=[CH:10]\[C:9](=[O:14])[NH:8][C:5](=[O:7])[NH2:6]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 76868N-Carbamylmaleimide

Product 1

HCID 5355044Ethylene glycol bismaleurateYield 79.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3 g of ethylene glycol (0.048 moles), 12 g of N-carbamylmaleimide (0.086 moles) and 0.3 g of zinc chloride (0.0022 moles) in 70 mL of acetonitrile was heated to reflux. After 3 hours, a lot of solid material had been produced from the mixture. The mixture was filtered and the solids washed with acetonitrile and dried to afford 11.7 g of ethylene glycol bismaleurate. M.P.: 158°-60° C.; 1H NMR (DMSO-d6): δ 10.5 (s, 2 H), 7.2-7.8 (m, 4 H), 6.2-6.4 (m, 4 H), 4.3 (s, 4 H).

Workup

  1. temperaturewas heated to reflux
  2. customa lot of solid material had been produced from the mixture
  3. filtrationThe mixture was filtered
  4. washthe solids washed with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-61b5383cd87642dcb05ed0d82f9fa92e
Source dataset
uspto-grants-2000_11
Patent number
US06150460

Reaction notes

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