Hydrochloric Acid → Methyl 3,5-dioxo-1,2,4-triazolidine-4-acetate

HRID 1660120Notes

Reaction equation

HRID 1660120 reaction equation
C(O[C:4]([NH:6][NH:7][C:8]([NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:9])=[O:5])C.Cl>[OH-].[K+]>[O:9]=[C:8]1[N:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:4](=[O:5])[NH:6][NH:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 205575511-Ethoxycarbonyl-4-methoxycarbonylmethyl-semicarbazide

Product 1

HCID 53759869Methyl 3,5-dioxo-1,2,4-triazolidine-4-acetateYield 35%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

27.47 g (0.125 mol) of 1-ethoxycarbonyl-4-methoxycarbonylmethyl-semicarbazide were dissolved in 95 ml (0.38 mol) of 4-M potassium hydroxide solution and heated on a steam-bath for 1.5 hours. The resulting solution was cooled to room temperature, acidified to pH 1 with concentrated hydrochloric acid and evaporated in vacuo to give a colourless solid. This solid was extracted with three 90 ml portions of boiling methanol. The extracts were filtered, combined and added to 400 ml of methanolic hydrogen chloride. The mixture was left to stand at room temperature overnight and then evaporated in vacuo to give a colourless solid. This solid was recrystallized from methanol to give 7.50 g (35%) of methyl 3,5-dioxo-1,2,4-triazolidine-4-acetate of melting point 215°-218° C.

Workup

  1. temperatureheated on a steam-bath for 1.5 hours
  2. customevaporated in vacuo
  3. customto give a colourless solid
  4. extractionThis solid was extracted with three 90 ml portions of boiling methanol
  5. filtrationThe extracts were filtered
  6. additionadded to 400 ml of methanolic hydrogen chloride
  7. waitThe mixture was left
  8. customevaporated in vacuo
  9. customto give a colourless solid
  10. customThis solid was recrystallized from methanol

Sources & evidence

ORD record
ord-0907ea3a66b145ce95686e73e893d4f9
Source dataset
uspto-grants-1981_12
Patent number
US04307094

Reaction notes

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