Trichloromethanesulfenyl chloride → HCID 20356001, compound

HRID 371712Notes

Reaction equation

HRID 371712 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[N:10]([CH3:13])[NH:9][C:8]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[Cl:17][C:18]([Cl:22])([Cl:21])[S:19]Cl>O>[C:1]1([N:7]2[C:11](=[O:12])[N:10]([CH3:13])[N:9]([S:19][C:18]([Cl:22])([Cl:21])[Cl:17])[C:8]2=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 178249Bicarbamimide, 2-methyl-N-phenyl-

Product 1

HCID 20356001HCID 20356001, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 38.2g (0.2 mole) 4-phenyl-1-methyl urazole in 200 ml water was added a solution of 8g (0.2 mole) sodium hydroxide in 20 ml water. A mixture of 37.2g (0.2 mole) trichloromethylsulfenyl chloride and 3g of an emulsifier solution (as in example 1) in 25 ml water was then 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 washed with water. After drying and recrystallizing from benzene-cyclohexane (1:1, by volume) there was obtained 65g (91%) 4-phenyl-1-methyl-2-(trichloromethylthio) urazole having a melting point of 154° C.

Workup

  1. additionwas then 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 washed with water
  7. customAfter drying
  8. customrecrystallizing from benzene-cyclohexane (1:1, by volume) there

Sources & evidence

ORD record
ord-f7138ef1e7504324a24a35a761f7db48
Source dataset
uspto-grants-1978_05
Patent number
US04087534

Reaction notes

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