Trichloromethanesulfenyl chloride → HCID 13711662, compound

HRID 745971Notes

Reaction equation

[CH2:1]([N:3]1[C:9]([CH3:11])([CH3:10])[C:7](=[O:8])[NH:6][C:4]1=[O:5])[CH3:2].[Cl:12][C:13]([Cl:17])([Cl:16])[S:14]Cl.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[CH2:1]([N:3]1[C:9]([CH3:10])([CH3:11])[C:7](=[O:8])[N:6]([S:14][C:13]([Cl:17])([Cl:16])[Cl:12])[C:4]1=[O:5])[CH3:2]

Participants

Conditions

Temperature: 7 °C

Procedure

A mixture of 15.6 g (0.1 mole) 1-ethyl-5,5-dimethylhydantoin (the product of Example 3), 19.5 g (0.1 moles) trichloromethylsulfenyl chloride and 1.2 g Aliquat® 336 in 100 ml methylene chloride was stirred vigorously for about 10 minutes. The reaction mixture was cooled to about 7° C. in an ice bath; 25 g (0.125 moles) of pre-cooled 20% aqueous sodium hydroxide were added at once. After the addition, the temperature of the reaction mixture rose to 27° C.; when the temperature returned to about 7° C., the ice bath was removed. The reaction mixture was washed three times with 50 ml ice water, dried over magnesium sulfate and stripped to give a solid. The solid was crystallized twice from toluene with charcoal treatment to give 16.0 g of the above-identified product as a white solid, melting point 141°-142° C.

Workup

additionAfter the addition
customrose to 27° C.
customreturned to about 7° C.
customthe ice bath was removed
washThe reaction mixture was washed three times with 50 ml ice water
dry with materialdried over magnesium sulfate
customto give a solid
customThe solid was crystallized twice from toluene with charcoal treatment

Sources & evidence

ORD record: ord-fe9b2a24d3024b479b1cfafec4127a68
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04602029

Reaction notes

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