4-(3,5-Dichlorophenyl)-1-(methoxycarbonyl)semicarbazide → 4-(3,5-Dichlorophenyl)-1,2,4-triazolidine-3,5-dione

HRID 1838459Notes

Reaction equation

HRID 1838459 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:17])[NH:11][NH:12][C:13](OC)=[O:14])[CH:5]=[C:6]([Cl:8])[CH:7]=1>[OH-].[K+]>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]2[C:10](=[O:17])[NH:11][NH:12][C:13]2=[O:14])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 1

HCID 172693274-(3,5-Dichlorophenyl)-1-(methoxycarbonyl)semicarbazide

Product 1

HCID 187550094-(3,5-Dichlorophenyl)-1,2,4-triazolidine-3,5-dioneYield 100.7%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A suspension of 4-(3,5-dichlorophenyl)-1-(methoxycarbonyl)semicarbazide (30.3 g, 109 mmol) (Preparation 2) in KOH (54.5 ml, 4M) was heated under reflux for 1 h. After cooling to RT, the insoluble material was discarded and the filtrate acidified to pH 1-2. The precipitate was filtered, washed with water and pentane, and oven dried to yield the above compound as a white solid (27 g, mp=260° C.). 1H NMR (DMSO-d6): 10.80 (2H, s), 7.66 (3H, m).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. filtrationThe precipitate was filtered
  4. washwashed with water and pentane, and oven
  5. customdried

Sources & evidence

ORD record
ord-e24608ff52044589bba9441dcb745541
Source dataset
uspto-grants-2004_01
Patent number
US06673825B2

Reaction notes

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