Dimethyl Sulfoxide → HCID 178473062, compound

HRID 2052243Notes

Reaction equation

HRID 2052243 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6]([CH2:8][O:9][CH2:10][C:11]([NH:13][NH2:14])=[O:12])=[O:7])[CH3:4].[C:15](=S)=[S:16].CS(C)=O>C(O)C.O>[CH2:3]([O:5][C:6]([CH2:8][O:9][CH2:10][C:11]1[O:12][C:15]([SH:16])=[N:14][N:13]=1)=[O:7])[CH3:4]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 20377449HCID 20377449, compound

Product 1

HCID 178473062HCID 178473062, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (0.22 g.) in ethanol (2.5 ml.) was added to a suspension of ethoxycarbonylmethoxyacetohydrazide in ethanol (4 ml.), followed by the addition of carbon disulfide (0.95 ml.) and dimethyl sulfoxide (0.54 ml.), respectively. The reaction mixture was then refluxed for a period of 12 hours, cooled and filtered, and the resulting filtrate subsequently evaporated in vacuo. The residual oil so obtained was then dissolved in water, filtered and the filtrate acidifed to pH 2.0 with aqueous 2N hydrochloric acid. Extraction of the latter solution with ethyl acetate and subsequent evaporation of the solvent then yielded the desired product, viz., 2-(ethoxycarbonylmethoxymethyl)-1,3,4-oxadiazole-5-thiol, as a white solid material (yield, 0.5 g.), m.p. 101°-103° C.

Workup

  1. temperatureThe reaction mixture was then refluxed for a period of 12 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe resulting filtrate subsequently evaporated in vacuo
  5. customThe residual oil so obtained
  6. filtrationfiltered
  7. extractionExtraction of the latter solution
  8. customwith ethyl acetate and subsequent evaporation of the solvent

Sources & evidence

ORD record
ord-3d6895b8c65e42bd8305b77d8c118273
Source dataset
uspto-grants-1980_01
Patent number
US04183925

Reaction notes

Loading…