Water → 5-Ethyl-5-(3-azidopropyl)barbituric acid

HRID 1534002Notes

Reaction equation

HRID 1534002 reaction equation
[CH2:1]([C:3]1([CH2:12][CH2:13][CH2:14]Br)[C:8](=[O:9])[NH:7][C:6](=[O:10])[NH:5][C:4]1=[O:11])[CH3:2].[N-:16]=[N+:17]=[N-:18].[Na+].O>CC(C)=O>[CH2:1]([C:3]1([CH2:12][CH2:13][CH2:14][N:16]=[N+:17]=[N-:18])[C:8](=[O:9])[NH:7][C:6](=[O:10])[NH:5][C:4]1=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 199118015-Ethyl-5-(3-bromopropyl)barbituric acid

Product 1

HCID 199117995-Ethyl-5-(3-azidopropyl)barbituric acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 30 g of 5-ethyl-5-(3-bromopropyl) barbituric acid and 13 g of sodium azide in 350 ml of acetone was added to 240 ml of water and refluxed for approximately 18 hours. Thereafter, the solution was cooled on ice, filtered, air dried, and dissolved in a minimal amount of hot 95% ethanol. Crystals appeared after cooling and were filtered and air-dried. The melting point was 182°-184° C.

Workup

  1. temperaturerefluxed for approximately 18 hours
  2. temperatureThereafter, the solution was cooled on ice
  3. filtrationfiltered
  4. customair dried
  5. dissolutiondissolved in a minimal amount of hot 95% ethanol
  6. temperatureafter cooling
  7. filtrationwere filtered
  8. customair-dried

Sources & evidence

ORD record
ord-7932057a12ca4f64a38f1bdc24e7db33
Source dataset
uspto-grants-1992_02
Patent number
US05086167

Reaction notes

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