Methanol → methyl 2-[(cyanomethyl)thio]acetate

HRID 1763387Notes

Reaction equation

HRID 1763387 reaction equation
CO[C:3](=[S:5])C.[CH3:6][O-:7].[Na+].Cl[CH2:10][C:11]#[N:12].[CH3:13][OH:14]>>[CH3:6][O:7][C:13](=[O:14])[CH2:3][S:5][CH2:10][C:11]#[N:12]

Participants

5

Reactant 4

HCID 887MethanolHCID 7856ChloroacetonitrileHCID 519840Methyl thioacetateHCID 10942334Sodium Methoxide

Product 1

HCID 2778540methyl 2-[(cyanomethyl)thio]acetate

Procedure

- 31.8 g. (0.3 mol.) of thioacetic acid methyl ester are added to 150 ml. (0.3 mol.) of 2N sodium methylate solution. 22.6 g. (0.3 mol.) of chloroacetonitrile dissolved in 30 ml. of methanol are added dropwise while cooling and stirring. It is stirred overnight then refluxed for 30 minutes. The reaction mixture is cooled and the solvent is evaporated. 100 ml. of water are added to the residue and the aqueous solution is extracted twice with ether. The combined ether extracts are decolorized with activated carbon and dried with magnesium sulfate. The ether is distilled off and the residue is distilled under vacuum. 30.5 g. of 2-[(cyanomethyl)thio]acetic acid methyl ester are obtained b.p.10mm 132°-134°.

Workup

  1. temperaturewhile cooling
  2. stirringIt is stirred overnight
  3. temperaturethen refluxed for 30 minutes
  4. temperatureThe reaction mixture is cooled
  5. customthe solvent is evaporated
  6. additionof water are added to the residue
  7. extractionthe aqueous solution is extracted twice with ether
  8. dry with materialdried with magnesium sulfate
  9. distillationThe ether is distilled off
  10. distillationthe residue is distilled under vacuum

Sources & evidence

ORD record
ord-d057f1c76ce24822956eec62a889d852
Source dataset
uspto-grants-1978_09
Patent number
US04111978

Reaction notes

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