Water → HCID 86757520, compound

HRID 381699Notes

Reaction equation

HRID 381699 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:15][CH2:16][CH2:17][OH:18])(=[O:14])[CH:12]=[CH2:13].O>C(#N)C.[Cl-].[Zn+2].[Cl-]>[C:5]([OH:10])(=[O:14])/[CH:6]=[CH:7]\[C:8](=[O:9])[NH:4][C:1](=[O:3])[NH2:2].[C:11]([O:15][CH2:16][CH2:17][OH:18])(=[O:14])[CH:12]=[CH2:13]

Participants

6

Reactant 3

HCID 962WaterHCID 131652-Hydroxyethyl acrylateHCID 76868N-Carbamylmaleimide

Product 1

HCID 86757520HCID 86757520, compoundYield 167.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 140 g of N-carbamylmaleimide (1 mole), 121.8 g of 2-hydroxyethyl acrylate (1.05 moles) and 1.36 g of zinc chloride (0.01 moles) in 200 mL of acetonitrile was heated to reflux. After 5 hours, the mixture was poured into 500 mL of water. The solid was filtered, washed with water and dried to afford 240.7 g (94% yield) of 2-hydroxyethyl acrylate maleurate. M.P.: 88°-90° C. (dec.); 1H NMR (CDCl3): δ10.4 (br s, 1H), 8.2 (br s, 1H), 6.4 (m, 3H), 6.2 (d of d, 1H), 5.9 (m, 2H), 4.4 (A2B2, 4H); 13C NMR (CDCl3): δ165.9, 165.3, 165.2, 155.1, 133.1, 131.6, 129.5, 127.8, 63.2, 61.9; HPLC (10% CH3CN/H2O, C18): Rt=5.7 minutes.

Workup

  1. temperaturewas heated to reflux
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3e240dd648aa4ef2ac2e5e31d95c73ea
Source dataset
uspto-grants-2001_10
Patent number
US06307058B1

Reaction notes

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