1-Butanol → BUTYL MALEURATE

HRID 381694Notes

Reaction equation

HRID 381694 reaction equation
[C:1]([N:4]1[C:8](=[O:9])[CH:7]=[CH:6][C:5]1=[O:10])(=[O:3])[NH2:2].[CH2:11](O)[CH2:12][CH2:13][CH3:14].[OH2:16]>[Cl-].[Zn+2].[Cl-].CC#N.O>[C:5]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:16])/[CH:6]=[CH:7]\[C:8](=[O:9])[NH:4][C:1](=[O:3])[NH2:2]

Participants

6

Reactant 3

HCID 2631-ButanolHCID 962WaterHCID 76868N-Carbamylmaleimide

Product 1

HCID 5355031BUTYL MALEURATEYield 93%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 140 g of N-carbamylmaleimide (1 mole), 1.36 g of zinc chloride (0.01 moles) and 150 g of n-butanol (2 moles) was heated to reflux. After 4 hours, the mixture was poured into 400 mL of water and cooled to room temperature. The butyl maleurate was filtered, washed with water and dried to afford 200 g (93% yield). M.P.: 97°-90° C.; 1H NMR (CDCl3): δ10.6 (brs, 1H), 8.2 (brs, 1H), 6.3 (AB, 2H), 5.9 (brs, 1H), 4.2 (t, 2H), 1.6 (m, 2H), 1.4 (m, 2H), 0.9 (t, 3H); HPLC (20 to 40% CH3CN/H2O over 20 minutes, C8): Rt=9.4 minutes.

Workup

  1. temperaturewas heated to reflux
  2. filtrationThe butyl maleurate was filtered
  3. washwashed with water
  4. customdried
  5. customto afford 200 g (93% yield)

Sources & evidence

ORD record
ord-ca77c181c8fa41388f31039661a1c18f
Source dataset
uspto-grants-2001_10
Patent number
US06307058B1

Reaction notes

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