Malonamide → HCID 178513833, compound

HRID 1604869Notes

Reaction equation

HRID 1604869 reaction equation
[CH2:1]([C:5]([NH2:7])=[O:6])[C:2]([NH2:4])=[O:3].C1(C)C=CC(S([N:17]=[N+:18]=[N-])(=O)=O)=CC=1>C(O)C>[OH:3][C:2]1[N:4]=[N:17][NH:18][C:1]=1[C:5]([NH2:7])=[O:6]

Participants

4

Reactant 2

HCID 7911Malonamide2×HCID 13661p-Toluenesulfonyl azide

Product 1

HCID 178513833HCID 178513833, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxide obtained from sodium (2.3 g, 0.10 mole) and absolute ethanol (150 ml) was added malondiamide (10.2 g, 0.10 mole). The mixture was stirred until most of the malondiamide dissolved. p-Toluenesulfonyl azide (19.7 g, 0.10 mole) was dissolved in ethanol (20 ml) and added dropwise with stirring. The thick mixture was stirred at room temperature for 30 min and heated under reflux in an oil bath for an additional 30 min. The mixture was cooled and the sodium salt was removed by filtration and washed with ethanol followed by ether. The salt was dissolved in a minimum of hot water and the solution was acidified to pH 2 with dilute hydrochloric acid. Upon cooling, the product crystallized. The compound was recrystallized from water to give 9.0 g of the known compound 4-hydroxy-1,2,3-triazole-5-carboxamide, m.p. 191°-192°.

Workup

  1. dissolutiondissolved
  2. additionadded dropwise
  3. stirringThe thick mixture was stirred at room temperature for 30 min
  4. temperatureheated
  5. temperatureunder reflux in an oil bath for an additional 30 min
  6. temperatureThe mixture was cooled
  7. customthe sodium salt was removed by filtration
  8. washwashed with ethanol
  9. dissolutionThe salt was dissolved in a minimum of hot water
  10. temperatureUpon cooling
  11. customthe product crystallized
  12. customThe compound was recrystallized from water

Sources & evidence

ORD record
ord-4bd67bb8d5c842169e2a07b1ddff3867
Source dataset
uspto-grants-1976_04
Patent number
US03948885

Reaction notes

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