Hydrochloric Acid → 2-(3,5-Dioxo-1,2,4-triazolidin-4-yl)acetic acid

HRID 1660121Notes

Reaction equation

HRID 1660121 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]([O:10]C)=[O:9])[C:5](=[O:12])[NH:4][NH:3]1.[OH-].[Na+].Cl>>[O:1]=[C:2]1[N:6]([CH2:7][C:8]([OH:10])=[O:9])[C:5](=[O:12])[NH:4][NH:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53759869Methyl 3,5-dioxo-1,2,4-triazolidine-4-acetate

Product 1

HCID 205575302-(3,5-Dioxo-1,2,4-triazolidin-4-yl)acetic acidYield 33%

Procedure

0.5 g (2.9 mmol) of methyl 3,5-dioxo-1,2,4-triazolidine-4-acetate was stirred at room temperature for 2 hours with 8.7 ml (8.7 mmol) of 1-M sodium hydroxide solution. The resulting solution was acidified with concentrated hydrochloric acid and evaporated to dryness. The solid residue was extracted with hot acetonitrile. The acetonitrile extracts were evaporated and the residual colourless solid was recrystallized from acetonitrile, there being obtained 0.15 g (33%) of 3,5-dioxo-1,2,4-triazolidine-4-acetic acid of melting point 220°-223° C. (from acetonitrile).

Workup

  1. customevaporated to dryness
  2. extractionThe solid residue was extracted with hot acetonitrile
  3. customThe acetonitrile extracts were evaporated
  4. customthe residual colourless solid was recrystallized from acetonitrile, there

Sources & evidence

ORD record
ord-75b26e5952c944288a2a8754a147d2d3
Source dataset
uspto-grants-1981_12
Patent number
US04307094

Reaction notes

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