Ethanethiol → HCID 86739595, compound

HRID 358331Notes

Reaction equation

HRID 358331 reaction equation
C([SH:3])C.C(N([CH2:9][CH3:10])CC)C.[Cl:11][C:12](Cl)=[C:13]([Cl:18])[C:14]([O:16][CH3:17])=O>CO.C(S)C>[CH3:17][O:16][C:14](=[S:3])[C:13]([Cl:18])=[C:12]([Cl:11])[CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 8471TriethylamineHCID 525088Methyl trichloropropenoate

Product 1

HCID 86739595HCID 86739595, compoundYield 104.3%

Reagents, catalysts & solvents 2

HCID 6343EthanethiolCatalystHCID 887MethanolSolvent

Procedure

A solution of 270 gms of ethanethiol and 580 ml (419 gms) of triethylamine in 1 liter of methanol was slowly added to 795 gms methyl trichloroacrylate. The addition was exothermic and cooling was required. After addition, the reaction mixture was stirred at room temperature for 18 hours. At this time, an additional 20 gms of ethanethiol was added and the system stirred for an additional 2 hours. The solvent and excess ethanethiol were removed under reduced pressure. The resulting oil was dissolved in methylene chloride. The organic solution was washed with water, dried over magnesium sulfate and filtered. The methylene chloride was removed by stripping to give 860 gms of a brown liquid. The crude product was purified by vacuum distillation to give 600 gms of the methyl-2,3-dichloro-3-ethylthioacrylate (collected at 135°-145° C. at 20 mm Hg).

Workup

  1. additionThe addition
  2. temperaturecooling
  3. additionAfter addition
  4. stirringthe system stirred for an additional 2 hours
  5. customThe solvent and excess ethanethiol were removed under reduced pressure
  6. dissolutionThe resulting oil was dissolved in methylene chloride
  7. washThe organic solution was washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customThe methylene chloride was removed

Sources & evidence

ORD record
ord-91215cc5ca5448469c442e0bdb1699eb
Source dataset
uspto-grants-1984_08
Patent number
US04466962

Reaction notes

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