Carbazic acid, dithio-, monopotassium salt (8CI) → Ethyl 5-sulfanyl-1,3,4-thiadiazole-2-carboxylate

HRID 1988203Notes

Reaction equation

HRID 1988203 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[C:5](SC)=S)[CH3:2].[NH:10]([C:12]([S-:14])=[S:13])[NH2:11].[K+]>C(O)C>[SH:13][C:12]1[S:14][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:9])=[N:11][N:10]=1

Participants

4

Reactant 2

HCID 10909709Carbazic acid, dithio-, monopotassium salt (8CI)HCID 12427868Ethyl (methylsulfanyl)(sulfanylidene)acetate

Product 1

HCID 178470473Ethyl 5-sulfanyl-1,3,4-thiadiazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl(methylthio)(thioxo)acetate (20.0 g, 122 mmol) and potassium hydrazinecarbodithioate (R. S. Drago et al., JACS (1983) 105, 2287) (17.8 g, 122 mmol) were reflux overnight in ethanol (500 ml). The solution was concentrated and EtOAc was added. The organic phase was washed with 1M HCl, brine and dried over anhydrous Na2SO4. The solvent was evaporated and the residue purified on silica gel (hexanes-acetone, 80:20) to give the title compound. 1H NMR (400 MHz, acetone-d6): 4.43 (q, 2H), 1.38 (t, 3H).

Workup

  1. concentrationThe solution was concentrated
  2. additionEtOAc was added
  3. washThe organic phase was washed with 1M HCl, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue purified on silica gel (hexanes-acetone, 80:20)

Sources & evidence

ORD record
ord-46f267bc728043b4ad6218c483c21f94
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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