p-Chlorothiophenol → HCID 13295544, compound

HRID 2290755Notes

Reaction equation

HRID 2290755 reaction equation
C[O-].[Na+].Cl[CH2:5][C:6]1([CH2:9][Cl:10])[CH2:8][O:7]1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1>C(#N)C>[Cl:10][CH2:9][C:6]1([CH2:5][S:18][C:15]2[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=2)[CH2:8][O:7]1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 10942334Sodium MethoxideHCID 127317282,2-Bis(chloromethyl)oxirane

Product 1

HCID 13295544HCID 13295544, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.4 g (0.1 mole) of sodium methylate are introduced in portions into a mixture of 16.9 g (0.12 mole) of 2,2-di(chloromethyl)-oxirane and 14.5 g (0.1 mole) of 4-chlorothiophenol in 200 ml of acetonitrile. The reaction mixture is subsequently stirred for 4 hours and filtered and the filtrate is concentrated in vacuo. The residue is dissolved in methylene chloride and the solution is washed with water, dried over sodium sulphate and concentrated. The oil which remains is distilled. 18.2 g (73% of theory) of 2-chloromethyl-2-(4-chlorophenylthiomethyl)-oxirane of refractive index nD20 1.5895 are obtained.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate is concentrated in vacuo
  3. dissolutionThe residue is dissolved in methylene chloride
  4. washthe solution is washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. distillationThe oil which remains is distilled

Sources & evidence

ORD record
ord-f527fb9ee82c4d52bb9ad8a0932a8f2b
Source dataset
uspto-grants-1986_10
Patent number
US04618619

Reaction notes

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