p-Chlorothiophenol → HCID 13295544, compound

HRID 649524Notes

Reaction equation

HRID 649524 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-0be63fc0eb0346dda277dc1d467da3f2
Source dataset
uspto-grants-1988_04
Patent number
US04740516

Reaction notes

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