Ethanol → 1-Allyl-6-ethoxy-4-methylhexahydropyrimidin-2-one

HRID 1607381Notes

Reaction equation

HRID 1607381 reaction equation
[CH2:1]([NH:4][C:5]([NH2:7])=[O:6])[CH:2]=[CH2:3].[CH:8](=[O:12])/[CH:9]=[CH:10]/[CH3:11].[CH3:13][CH2:14]O>Cl>[CH2:1]([N:4]1[CH:8]([O:12][CH2:13][CH3:14])[CH2:9][CH:10]([CH3:11])[NH:7][C:5]1=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 11181AllylureaHCID 447466Crotonaldehyde2×

Product 1

HCID 193761321-Allyl-6-ethoxy-4-methylhexahydropyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

Following a related procedure, [G. Zigeuner, W. Rauter, Monatshefte fur Chemie, 96, 1950 (1965)], allylurea (24.5 g, 0.25 mol), crotonaldehyde (19.67 g, 0.29 mol) and 37% HCl (12 drops) were mixed with 140 g of EtOH at room temperature for 3d, during which all of the crotonaldehyde was consumed. The major product had a retention time near that of allylurea. The dark mixture was neutralized with Na2CO3, filtered and concentrated at reduced pressure. Part of the crude mixture was extracted with cyclohexane, decolorized with charcoal, filtered and concentrated to give a light yellow oil which produced white crystals (mp 72°-76° C.) on standing. A separate sample was submitted to kugelrohr distillation (0.05 torr) to give further products: E at 90° C., F at 145°-155° C. (solid, mp 72°-76° C.) and G at 145°-155° C. (liquid).

Workup

  1. customwas consumed
  2. filtrationfiltered
  3. concentrationconcentrated at reduced pressure
  4. extractionPart of the crude mixture was extracted with cyclohexane
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a light yellow oil which

Sources & evidence

ORD record
ord-ec717c1fb8ff42f0bad35b17e9488a59
Source dataset
uspto-grants-1989_09
Patent number
US04864055

Reaction notes

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