1,1,2,2-Tetrachloroethylsulfenyl chloride → N-isopropyl-N-(trichlorovinylthio)-chloromethanesulfonamide

HRID 848398Notes

Reaction equation

HRID 848398 reaction equation
[CH:1]([NH:4][S:5]([CH2:8][Cl:9])(=[O:7])=[O:6])([CH3:3])[CH3:2].[Cl:10][C:11](Cl)([S:15]Cl)[CH:12]([Cl:14])[Cl:13]>C(N(CC)CC)C>[CH:1]([N:4]([S:15][C:11]([Cl:10])=[C:12]([Cl:14])[Cl:13])[S:5]([CH2:8][Cl:9])(=[O:7])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 3016718Methanesulfonamide, 1-chloro-N-(1-methylethyl)-

Product 1

HCID 12943924N-isopropyl-N-(trichlorovinylthio)-chloromethanesulfonamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 32.3 g (0.32 mol) sample of triethylamine was added dropwise to a cooled (0° C.) solution of 50 g (0.29 mol) N-isopropyl chloromethanesulfonamide and 70 g (0.29 mol) 1,1,2,2-tetrachloroethylsulfenyl chloride. After the addition was completed, the reaction was stirred at ambient temperature for 30 minutes and then under reflux for 3 hours. The reaction mixture was then cooled, washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give the N-isopropyl-N-(trichlorovinylthio)-chloromethanesulfonamide product, which after crystallization from pet. ether melted at 71°-73° C. The product is reported as Compound 1.

Workup

  1. additionAfter the addition
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction mixture was then cooled
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-92657f5fbe8d4675bd45b18191066f7c
Source dataset
uspto-grants-1981_10
Patent number
US04295874

Reaction notes

Loading…