Dimethyl Sulfoxide → HCID 178473062, compound

HRID 614229Notes

Reaction equation

HRID 614229 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 acidified to pH 2.0 with aqueous 2N hydrochloric acid. Extraction of the latter solution was 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. customethyl acetate and subsequent evaporation of the solvent

Sources & evidence

ORD record
ord-82fcadd05e244e69b0c820e91dabadc7
Source dataset
uspto-grants-1979_03
Patent number
US04144240

Reaction notes

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