Trichloromethanesulfenyl chloride → HCID 13711665, compound

HRID 745970Notes

Reaction equation

HRID 745970 reaction equation
[CH3:1][N:2]1[CH2:8][C:6](=[O:7])[NH:5][C:3]1=[O:4].[Cl:9][C:10]([Cl:14])([Cl:13])[S:11]Cl.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[CH3:1][N:2]1[CH2:8][C:6](=[O:7])[N:5]([S:11][C:10]([Cl:14])([Cl:13])[Cl:9])[C:3]1=[O:4]

Participants

6

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 692171-Methylhydantoin

Product 1

HCID 13711665HCID 13711665, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 11.4 g (0.1 mole) 1-methylhydantoin, 1.2 g Aliquat® 336 and 19.5 g (0.1 mole) trichloromethylsulfenyl chloride in 100 ml methylene chloride was stirred vigorously and cooled in an ice bath. To that mixture, 25 g of 20% pre-cooled aqueous sodium hydroxide was added at once; the temperature of the reaction mixture increased from 5° C. to 21° C. Stirring was continued; the ice bath was removed after 5 minutes. The methylene chloride layer was washed with water, dried over magnesium sulfate and stripped to give 24 g of sticky solids. Crystallization from toluene with charcoal treatment gave 8.4 g of the above-identified product, as a white solid, melting point 110°-112° C.

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added at once
  3. temperaturethe temperature of the reaction mixture increased from 5° C. to 21° C
  4. stirringStirring
  5. customthe ice bath was removed after 5 minutes
  6. washThe methylene chloride layer was washed with water
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-7b4536851b2e4577a6dfaf8ce47ecbe8
Source dataset
uspto-grants-1986_07
Patent number
US04602029

Reaction notes

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