Ethylene Glycol → Ethylene glycol bismaleurate

HRID 368919Notes

Reaction equation

HRID 368919 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-15b417e6bb3d4888bd3240ab5b991637
Source dataset
uspto-grants-2000_10
Patent number
US06136378

Reaction notes

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