Water → HCID 21487894, compound

HRID 1414539Notes

Reaction equation

HRID 1414539 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 three 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-f37a6b30768f42cfbaf41e04e1447fae
Source dataset
uspto-grants-1977_01
Patent number
US04001425

Reaction notes

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