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Trichloromethanesulfenyl chloride → 4-(3-Chlorophenyl)-1,2-bis-(trichloromethylthio) urazole

HRID 371708
Notes
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Reaction equation

HRID 371708 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[NH:11][NH:10][C:9]2=[O:14])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[Cl:17][C:18]([Cl:22])([Cl:21])[S:19]Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9](=[O:14])[N:10]([S:19][C:18]([Cl:22])([Cl:21])[Cl:17])[N:11]([S:19][C:18]([Cl:22])([Cl:21])[Cl:17])[C:12]2=[O:13])[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 12855214-(3-Chlorophenyl)-1,2,4-triazolidine-3,5-dione

Product 1

HCID 203560074-(3-Chlorophenyl)-1,2-bis-(trichloromethylthio) urazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 42.2g (0.2 mole) 4-(3-chlorophenyl) 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 (as in example 1) 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 cyclohexane there was obtained 70g (69%) 4-(3-chlorophenyl)-1,2-bis-(trichloromethylthio) urazole having a melting point of 153° 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 cyclohexane

Sources & evidence

ORD record
ord-8e2eb88ab11d40b1a7e10e885feceab1
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04087534

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes