Trichloromethanesulfenyl chloride → HCID 13711663, compound

HRID 745972Notes

Reaction equation

HRID 745972 reaction equation
[C:1]1([N:7]2[CH:13]([CH3:14])[C:11](=[O:12])[NH:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:15][C:16]([Cl:20])([Cl:19])[S:17]Cl.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[C:1]1([N:7]2[CH:13]([CH3:14])[C:11](=[O:12])[N:10]([S:17][C:16]([Cl:20])([Cl:19])[Cl:15])[C:8]2=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 28298275-methyl-1-phenylimidazolidine-2,4-dione

Product 1

HCID 13711663HCID 13711663, compoundYield 108.7%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 8.0 g (0.042 mole) 1-phenyl-5-methylhydantoin, 8.6 g (0.046 mole) trichloromethylsulfenyl chloride and 1.0 g Aliquat® 336 in 100 ml methylene chloride was cooled in an ice bath. To that mixture a pre-cooled sodium hydroxide solution (4.2 g of 50% sodium hydroxide diluted to 20 g with water) was added at once. The temperature of the reaction mixture rose from 3° C. to 5° C.; stirring was continued for 10 minutes. The methylene chloride layer was separated and washed well with water, dried over magnesium sulfate and stripped to give 15.5 g of an oil. After being washed with cold hexane, the oil slowly solidified. The solid was crystallized from hexane-toluene to give 9.9 g of the above-identified product as a white solid, melting point 113°-114° C.

Workup

  1. temperaturewas cooled in an ice bath
  2. customrose from 3° C. to 5° C.
  3. customThe methylene chloride layer was separated
  4. washwashed well with water
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-180947404a6541e1b22023328fe4a58d
Source dataset
uspto-grants-1986_07
Patent number
US04602029

Reaction notes

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