Pyridine → HCID 20306506, compound

HRID 1732449Notes

Reaction equation

HRID 1732449 reaction equation
[CH3:1][S:2]([C:4]([S:19][CH3:20])=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)=O.N1C=CC=CC=1.S(Cl)([Cl:29])=O>C(Cl)Cl>[CH3:1][S:2][C:4]([S:19][CH3:20])=[C:5]([Cl:29])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 54558564HCID 54558564, compound

Product 1

HCID 20306506HCID 20306506, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1-Methylsulfinyl-1-methylthio-2-(m-phenoxyphenyl)ethylene (4.56 g) was dissolved in 40 ml of methylene chloride, and 2 ml of pyridine was added. With stirring under ice cooling, 10 ml of a methylene chloride solution of 2.15 g of thionyl chloride was added dropwise over the course of 5 minutes. The mixture was further stirred for 1 hour under ice cooling, and methylene chloride was added in an amount sufficient to adjust the total amount of the mixture to 80 ml. The mixture was then washed three times with 20 ml of water. The product was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a Florisil column using hexane/benzene as an eluant to afford 3.403 g of 1,1-bis(methylthio)-2-chloro-2-(m-phenoxyphenyl)-ethylene as an oil in a yield of 70%. Samples for analysis were obtained by short-path distillation of this product [160°-180° C. (bath temperature)/0.01 mmHg].

Workup

  1. stirringThe mixture was further stirred for 1 hour under ice cooling
  2. washThe mixture was then washed three times with 20 ml of water
  3. dry with materialThe product was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on a Florisil column

Sources & evidence

ORD record
ord-3348a80b2b414e7bb9961c39e0c19002
Source dataset
uspto-grants-1980_12
Patent number
US04237298

Reaction notes

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