Water → 1-Ethoxycarbonyl-4-(3',5'-dichlorophenyl) urazole

HRID 371984Notes

Reaction equation

HRID 371984 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[NH:12][NH:11][C:10]2=[O:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(CC)CC)C.[CH2:23]([O:25][C:26](Cl)=[O:27])[CH3:24].O>CN(C)C=O>[CH2:23]([O:25][C:26]([N:12]1[C:13](=[O:14])[N:9]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)[C:10](=[O:15])[NH:11]1)=[O:27])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 187550094-(3,5-Dichlorophenyl)-1,2,4-triazolidine-3,5-dione

Product 1

HCID 544115751-Ethoxycarbonyl-4-(3',5'-dichlorophenyl) urazoleYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.5 g of 4-(3',5'-dichlorophenyl) urazole and 1 g of triethylamine in 10 ml of N,N-dimethylformamide was added dropwise 1.1 g of ethylchloroformate with agitation. The reaction and agitation were continued at room temperature for one hour. The reaction mass was mixed with water to precipitate crystals which were filtered and recrystallized from acetone-ethanol to obtain 2.3 g of 1-ethoxycarbonyl-4-(3',5'-dichlorophenyl) urazole, which constituted a yield of 72%.

Workup

  1. customThe reaction and agitation
  2. customto precipitate crystals which
  3. filtrationwere filtered
  4. customrecrystallized from acetone-ethanol

Sources & evidence

ORD record
ord-4ad44a5f61724d849663eb10b425cc2c
Source dataset
uspto-grants-1978_05
Patent number
US04088767

Reaction notes

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