Potassium Hydroxide → 4-(2-Chloroethyl)-1,2,4-triazolidine-3,5-dione

HRID 1660123Notes

Reaction equation

HRID 1660123 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5](=[O:13])[NH:6][NH:7][C:8](OCC)=[O:9].[OH-].[K+]>O>[Cl:1][CH2:2][CH2:3][N:4]1[C:5](=[O:13])[NH:6][NH:7][C:8]1=[O:9]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13144508HCID 13144508, compound

Product 1

HCID 131445094-(2-Chloroethyl)-1,2,4-triazolidine-3,5-dioneYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

23.9 g (0.114 mol) of 4-(2-chloroethyl)-1-ethoxycarbonyl-semicarbazide and 57 ml (0.228 mol) of 4-M potassium hydroxide solution were stirred together at room temperature for 2 hours. The mixture was diluted with 100 ml of water, applied to an ion-exchange column (Dowex 50X-8, H+ form) and eluted with water. The eluate was evaporated in vacuo to give a colourless solid which was recrystallized from water to give 7.97 g (43%) of 4-(2-chloroethyl)-1,2,4-triazolidine-3,5-dione of melting point 192°-193° C.

Workup

  1. washeluted with water
  2. customThe eluate was evaporated in vacuo
  3. customto give a colourless solid which
  4. customwas recrystallized from water

Sources & evidence

ORD record
ord-3a2c1e45fbd4422ab88f2476d30737e9
Source dataset
uspto-grants-1981_12
Patent number
US04307094

Reaction notes

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