Trichloromethanesulfenyl chloride → 4-Phenyl-1,2-bis[(trichloromethyl)sulfanyl]-1,2,4-triazolidine-3,5-dione

HRID 371707

Reaction equation

HRID 371707 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[NH:10][NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[Cl:16][C:17]([Cl:21])([Cl:20])[S:18]Cl>O>[C:1]1([N:7]2[C:8](=[O:13])[N:9]([S:18][C:17]([Cl:21])([Cl:20])[Cl:16])[N:10]([S:18][C:17]([Cl:21])([Cl:20])[Cl:16])[C:11]2=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 852294-Phenylurazole

Product 1

HCID 203560124-Phenyl-1,2-bis[(trichloromethyl)sulfanyl]-1,2,4-triazolidine-3,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 35.4g (0.2 mole) 4-phenyl urazole in 200 ml water was added a solution of 16g (0.4 mole) sodium hydroxide in 20 ml water. A mixture of 74.4g (0.4 mole)trichloromethylsulfenyl chloride and 3g of an emulsifier solution (EXEM 25, consisting of a mixture of alkyl benzene sulfonate and ethoxylated vegetable oil) in 50 ml water was added dropwise to the above basic solution while keeping the reaction mixture at 0° C. The reactants were mixed so that the reaction mixture was kept at a pH greater than 7. The precipitate that formed was filtered and the filter cake was washed with water. After drying and recrystallizing from benzene there was obtained 4-phenyl-1,2-bis-(trichloromethylthio)urazole having a melting point of 175° C.

Workup

  1. additionwas added dropwise to the above basic solution
  2. customat 0° C
  3. additionThe reactants were mixed so that the reaction mixture
  4. customThe precipitate that formed
  5. filtrationwas filtered
  6. washthe filter cake was washed with water
  7. customAfter drying
  8. customrecrystallizing from benzene

Sources & evidence

ORD record
ord-5e487487e6ed4ba898b9d3c8a62113dd
Source dataset
uspto-grants-1978_05
Patent number
US04087534

Linked notes

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