Carbon Disulfide → 5-cyclopropyl-1,3,4-oxadiazole-2-thiol

HRID 615601Notes

Reaction equation

HRID 615601 reaction equation
[CH:1]1([C:4]([NH:6][NH2:7])=[O:5])[CH2:3][CH2:2]1.[C:8](=S)=[S:9]>CN(C)C=O>[SH:9][C:8]1[O:5][C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:6][N:7]=1

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 81396Cyclopropanecarbohydrazide

Product 1

HCID 1785279325-cyclopropyl-1,3,4-oxadiazole-2-thiol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 17.9 g (0.179 mole) cyclopropane carboxylic acid hydrazide (the product of Example 6) in about 75 ml dimethylformamide, 68.0 g (0.894 mole) carbon disulfide was added (and all solids dissolved). The solution turned orange and then green. The reaction mixture was stirred about 1 hour at room temperature, refluxed about 3 hours, and stirred overnight at room temperature. The mixture was added to an ice-water bath to give an oil. The mixture was extracted with methylene chloride. The methylene chloride fraction was dried over magnesium sulfate and stripped. Chromatography on silica gel, eluting with methylene chloride, gave the above-identified product as a solid, melting point 76°-78° C.

Workup

  1. dissolutiondissolved)
  2. temperaturerefluxed about 3 hours
  3. stirringstirred overnight at room temperature
  4. additionThe mixture was added to an ice-water bath
  5. customto give an oil
  6. extractionThe mixture was extracted with methylene chloride
  7. dry with materialThe methylene chloride fraction was dried over magnesium sulfate
  8. washChromatography on silica gel, eluting with methylene chloride

Sources & evidence

ORD record
ord-217e16b2919a4951aa7634417f410af0
Source dataset
uspto-grants-1985_02
Patent number
US04500539

Reaction notes

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