2-Hydroxyethyl Methacrylate → HCID 86757521, compound

HRID 381700Notes

Reaction equation

HRID 381700 reaction equation
[C:1]([N:4]1[C:8](=[O:9])[CH:7]=[CH:6][C:5]1=[O:10])(=[O:3])[NH2:2].[C:11]([O:16][CH2:17][CH2:18][OH:19])(=[O:15])[C:12]([CH3:14])=[CH2:13]>C(#N)C.[Cl-].[Zn+2].[Cl-]>[C:5]([OH:10])(=[O:15])/[CH:6]=[CH:7]\[C:8](=[O:9])[NH:4][C:1](=[O:3])[NH2:2].[C:11]([O:16][CH2:17][CH2:18][OH:19])(=[O:15])[C:12]([CH3:14])=[CH2:13]

Participants

5

Reactant 2

HCID 133602-Hydroxyethyl MethacrylateHCID 76868N-Carbamylmaleimide

Product 1

HCID 86757521HCID 86757521, compoundYield 138.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 140 g of N-carbamylmaleimide (1 mole), 130 g of 2-hydroxyethyl methacrylate (1 mole) and 1.36 g of zinc chloride (0.01 moles) in 200 mL of acetonitrile was heated to reflux. After 6 hours, the acetonitrile was evaporated and 500 mL of H2O was added. The solid was filtered and dried to afford 200 g (74% yield) of 2-hydroxyethyl methacrylate maleurate. M.P.: 62°-4° C. (dec.); 1H NMR (CDCl3): δ10.5 (br s, 1H), 8.2 (br s, 1H), 6.4 (m, 2H), 6.1 (m, 1H), 5.8 (br s, 1H), 5.6 (m, 1H), 4.4 (A2B2, 4H), 2.0 (m, 3H); 13C (CDCl3): δ167.1, 165.24, 165.23, 155.1, 135.8, 132.9, 129.6, 126.2, 63.2, 62.0, 18.2; HPLC (20% CH3CN/H2O, C18): Rt=3.5 minutes.

Workup

  1. temperaturewas heated to reflux
  2. customthe acetonitrile was evaporated
  3. addition500 mL of H2O was added
  4. filtrationThe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-a3f0bb511c3649ce83d8cb65835bb26a
Source dataset
uspto-grants-2001_10
Patent number
US06307058B1

Reaction notes

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