Water → HCID 21487894, compound

HRID 918076Notes

Reaction equation

HRID 918076 reaction equation
[O:1]1[CH2:5][C:4](=O)[CH2:3][C:2]1=[O:7].[C:8]([NH:13][C:14]([NH2:16])=[O:15])([CH2:11][CH3:12])([CH3:10])[CH3:9].O>C1C=CC=CC=1>[C:8]([NH:13][C:14]([NH:16][C:4]1[CH2:5][O:1][C:2](=[O:7])[CH:3]=1)=[O:15])([CH2:11][CH3:12])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 69363Urea, (1,1-dimethylpropyl)-HCID 521261Tetronic acid

Product 1

HCID 21487894HCID 21487894, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3 g of 2,4-furandione in 100 ml of benzene is added 4 g of tert-amylurea. The solution is heated under nitrogen at reflux for 3 hours with water removal. At the end of that period the solution is cooled and concentrated. The residual material is recrystallized from acetonitrile to give 2.5 g of 1-tert-amyl-3-(2,5-dihydro-5-oxo-3-furyl)urea, m.p. 169°-171°C. The infrared and n.m.r. spectra are consistent with the assigned structure.

Workup

  1. temperatureThe solution is heated under nitrogen
  2. temperatureAt the end of that period the solution is cooled
  3. concentrationconcentrated
  4. customThe residual material is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c04f4fb1ccdf405e9417be25f0046ec2
Source dataset
uspto-grants-1976_07
Patent number
US03969370

Reaction notes

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