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

HRID 371709

Reaction equation

HRID 371709 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[NH:11][NH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:17][C:18]([Cl:22])([Cl:21])[S:19]Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([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:6][CH:7]=1

Participants

5

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 53055984-(4-Chlorophenyl)-1,2,4-triazolidine-3,5-dione

Product 1

HCID 203559844-(4-Chlorophenyl)-1, 2-bis(trichloromethylthio)urazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 42.2g (0.2 mole) 4-(4-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 was formed was collected on a filter and the filter cake was washed with water. After drying, triturating with ethyl ether, and recrystallizing from benzene-cyclohexane (1:1, by volume) there was obtained 42g (64%) of 4-(4-chlorophenyl)-1, 2-bis(trichloromethylthio)urazole having a melting point of 169° 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 was formed
  5. customwas collected on
  6. filtrationa filter
  7. washthe filter cake was washed with water
  8. customAfter drying
  9. customtriturating with ethyl ether
  10. customrecrystallizing from benzene-cyclohexane (1:1, by volume) there

Sources & evidence

ORD record
ord-6c4eac9d8d0b46a889b1b73f58176d25
Source dataset
uspto-grants-1978_05
Patent number
US04087534

Linked notes

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