Barbituric Acid → 5-(3,5-Dibromo-2-hydroxybenzylidene) perhydropyrimidine-2,4,6-trione

HRID 55769

Reaction equation

HRID 55769 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[Br:10][C:11]1[C:12]([OH:20])=[C:13]([CH:16]=[C:17]([Br:19])[CH:18]=1)[CH:14]=O>C(O)(=O)C>[Br:10][C:11]1[C:12]([OH:20])=[C:13]([CH:16]=[C:17]([Br:19])[CH:18]=1)[CH:14]=[C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][C:8]1=[O:9]

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 70243,5-Dibromosalicylaldehyde

Product 1

HCID 733338665-(3,5-Dibromo-2-hydroxybenzylidene) perhydropyrimidine-2,4,6-trioneYield 84.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.01 mol (1.28 g) of barbituric acid (5a) were dissolved in 25 ml of glacial acetic acid while heating. Then 0.011 mol (3.08 g) of 3,5-dibromo-2-hydroxybenzaldehyde (6a) were added to the obtained solution while stirring and the resulting reaction mixture was left at room temperature during 36 hours. The produced crystal product was filtered, washed with cold acetic acid, then washed with ether and air-dried. Thereby 3.3 g of product 1a were obtained in the form of yellow needle crystals with melting temperature of 255-260° C. (with decomposition). Output amounted to 77% of the theoretical value.

Workup

  1. temperaturewhile heating
  2. customthe resulting reaction mixture
  3. filtrationThe produced crystal product was filtered
  4. washwashed with cold acetic acid
  5. washwashed with ether
  6. customair-dried

Sources & evidence

ORD record
ord-ff8c21361d14437684a0e5ae9d9179b4
Source dataset
uspto-grants-2016_09
Patent number
US09433623B2

Linked notes

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