Ethyl oxamate → ethyl 2-oxo-2H-1,3,4-oxathiazole-5-carboxylate

HRID 1764055Notes

Reaction equation

HRID 1764055 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([NH2:4])=[O:3].Cl[C:10]([S:12]Cl)=[O:11]>C1(C)C=CC=CC=1>[O:11]=[C:10]1[S:12][N:4]=[C:2]([C:1]([O:6][CH2:7][CH3:8])=[O:5])[O:3]1

Participants

4

Reactant 2

HCID 69238Ethyl oxamateHCID 75990(Chlorothio)formyl chloride

Product 1

HCID 12351252ethyl 2-oxo-2H-1,3,4-oxathiazole-5-carboxylateYield 64.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 99.7 g (0.85 mol) of ethyl oxamate and 552 g (4.23 mol) of chlorocarbonylsulfenyl chloride, prepared in accordance with British Pat. No. 1,079,348, in toluene was held at reflux for 5.25 hours and then was concentrated under vacuum. Benzene was added to the residue, and the solution was extracted twice with water, twice with 5% NaHCO3, again with water, and was dried (CaSO4) and concentrated under vacuum. The residual oil was filtered to remove sulfur and was crystallized twice from methylcyclohexane to give 95.61 g (64%) of white solid, mp 49°-50.5 C.

Workup

  1. customprepared in accordance with British Pat
  2. temperatureat reflux for 5.25 hours
  3. concentrationwas concentrated under vacuum
  4. additionBenzene was added to the residue
  5. extractionthe solution was extracted twice with water, twice with 5% NaHCO3, again with water
  6. dry with materialwas dried (CaSO4)
  7. concentrationconcentrated under vacuum
  8. filtrationThe residual oil was filtered
  9. customto remove sulfur
  10. customwas crystallized twice from methylcyclohexane

Sources & evidence

ORD record
ord-0528291c5d4b466f9304b7d585583c65
Source dataset
uspto-grants-1978_09
Patent number
US04115095

Reaction notes

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