Pyridine → HCID 12963243, compound

HRID 1973392Notes

Reaction equation

HRID 1973392 reaction equation
[S:1]([Cl:5])(Cl)(=O)=O.[CH3:6][C:7]1[CH:12]=[CH:11][C:10](S)=[CH:9][CH:8]=1.N1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:1][Cl:5]

Participants

6

Reactant 3

HCID 1049PyridineHCID 78114-MethylbenzenethiolHCID 24648Sulfuryl chloride

Product 1

HCID 12963243HCID 12963243, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 27.2 g of sulfuryl chloride in 50 ml of dry carbon tetrachloride was added dropwise to a cold (ice-salt bath) solution of 25 g of 4-methylbenzenethiol in 50 ml of carbon tetrachloride containing a few drops of pyridine. The solution was stirred for 0.5 hour at ice-salt bath temperature, allowed to warm to room temperature, then heated under gentle reflux for 0.5 hour. The solution was filtered through a layer of anhydrous sodium sulfate and the filtrate concentrated under reduced pressure. The red liquid residue was distilled to give 24.1 g of 2-methylbenzenesulfenyl chloride, b.p. 67°-69° at 2 mm, nD25 1.6015.

Workup

  1. temperatureheated
  2. temperatureunder gentle reflux for 0.5 hour
  3. filtrationThe solution was filtered through a layer of anhydrous sodium sulfate
  4. concentrationthe filtrate concentrated under reduced pressure
  5. distillationThe red liquid residue was distilled

Sources & evidence

ORD record
ord-b184a4b843a84eb2bf64c5375aa0c72d
Source dataset
uspto-grants-1976_12
Patent number
US03997549

Reaction notes

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