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

HRID 267727Notes

Reaction equation

HRID 267727 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-52e98f09db22491e9c2b2841aada0cca
Source dataset
uspto-grants-1976_03
Patent number
US03944546

Reaction notes

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