Trichloromethanesulfenyl chloride → HCID 23311298, compound

HRID 745974Notes

Reaction equation

HRID 745974 reaction equation
[CH3:1][O:2][CH:3]([N:5]1[CH:11]([CH3:12])[C:9](=[O:10])[NH:8][C:6]1=[O:7])[CH3:4].[Cl:13][C:14]([Cl:18])([Cl:17])[S:15]Cl.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[CH3:1][O:2][CH:3]([N:5]1[CH:11]([CH3:12])[C:9](=[O:10])[N:8]([S:15][C:14]([Cl:18])([Cl:17])[Cl:13])[C:6]1=[O:7])[CH3:4]

Participants

6

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 23311297HCID 23311297, compound

Product 1

HCID 23311298HCID 23311298, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 8.6 g (0.05 mole) 1-methoxyethyl-5-methylhydantoin (the product of Example 12), 10.2 g (0.055 mole) trichloromethylsulfenyl chloride and 1.0 g Aliquat® 336 in 100 ml methylene chloride was cooled in an ice bath. To that mixture a precooled sodium hydroxide solution (5.0 g of 50% sodium hydroxide diluted to 25 g) was added at once. After the addition, the temperature of the reaction mixture increased from 5° to 15° C. After 5 minutes the ice bath was removed; stirring was continued for about 25 minutes. The aqueous phase was separated. The organic phase was dried and stripped to give an oil. The oil was washed with hexane to give 14.1 g of a semi-solid. The semi-solid was taken up in 50 ml chloroform and applied to a column of 225 g silica gel; elution with 2% methanol in chloroform gave 10.1 g of the above-identified product as a viscous orange oil.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionAfter the addition
  3. temperaturethe temperature of the reaction mixture increased from 5° to 15° C
  4. customAfter 5 minutes the ice bath was removed
  5. customThe aqueous phase was separated
  6. customThe organic phase was dried
  7. customto give an oil
  8. washThe oil was washed with hexane

Sources & evidence

ORD record
ord-cbe74cb898c1471cb0988c0be3345637
Source dataset
uspto-grants-1986_07
Patent number
US04602029

Reaction notes

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