Hydrogen Sulfide → HCID 19849194, compound

HRID 1608345Notes

Reaction equation

HRID 1608345 reaction equation
[OH-].[K+].[SH2:3].Cl[C:5]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[N:6][N:7]=[CH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1>C(O)C>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:5]2[S:3][CH:8]([C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:7][N:6]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 14797Potassium HydroxideHCID 53795609HCID 53795609, compound

Product 1

HCID 19849194HCID 19849194, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6.7 g (0.1 mole) of 85 % potassium hydroxide in 190 ml of ethanol which has been freshly saturated with hydrogen sulfide are added 24.3 g (0.1 mole) of 1-chloro-1,4-bis(pyrid-3-yl)-2,3-diazabutadiene at low temperature. After 2 hours the solvent is removed by evaporation under vacuum and the residue is dissolved in ethyl acetate. The ethyl acetate solution is washed with water and with a saturated solution of sodium chloride, then dried over sodium sulfate, filtered, and the filtrate is concentrated by evaporation. The residue is stirred in hexane/ether, filtered, washed and dried, affording 2,5-bis(pyrid-3-yl)-4,5-dihydro-1,3,4-thiadiazole of formula ##STR11## with a melting point of 77°-78° C.

Workup

  1. customAfter 2 hours the solvent is removed by evaporation under vacuum
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washThe ethyl acetate solution is washed with water and with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated by evaporation
  7. filtrationfiltered
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-0f34d323eb6f483db5465e0dbbfd5f81
Source dataset
uspto-grants-1989_09
Patent number
US04870184

Reaction notes

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