Pyridine → HCID 14883432, compound

HRID 1710045Notes

Reaction equation

HRID 1710045 reaction equation
[CH3:1][N:2]([C:4]([NH:6][CH3:7])=[S:5])[NH2:3].N1C=CC=CC=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](Cl)=[O:20]>CCOCC>[CH3:1][N:2]([C:4]([NH:6][CH3:7])=[S:5])[NH:3][C:19]([C:15]1[S:14][CH:18]=[CH:17][CH:16]=1)=[O:20]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 789282-Thiophenecarbonyl chlorideHCID 30341872,4-Dimethylthiosemicarbazide

Product 1

HCID 14883432HCID 14883432, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred, room temperature, solution of 2,4-dimethylthiosemicarbazide (3.75 g, 3.15×10-2 mole) and pyridine (30 ml) was added dropwise 2-thiophenecarbonyl chloride (3.20 ml, 2.99×10-2 mole). After stirring overnight the pyridine was evaporated at reduced pressure and the concentrate was treated with H2O. The resulting semi-solid was extracted into ethyl acetate. The ethyl acetate extract was washed with saturated NaCl and subsequently dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure, leaving a slightly yellowish solid. This was treated with Et2O and the solid was collected by filtration affording a colorless powder: 4.7 g (68%), mp 176°-178° C.

Workup

  1. customwas evaporated at reduced pressure
  2. additionthe concentrate was treated with H2O
  3. extractionThe resulting semi-solid was extracted into ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with saturated NaCl
  6. dry with materialsubsequently dried over anhydrous Na2SO4
  7. customThe drying agent was removed by filtration
  8. customthe filtrate was evaporated at reduced pressure
  9. customleaving a slightly yellowish solid
  10. filtrationthe solid was collected by filtration
  11. customaffording a colorless powder

Sources & evidence

ORD record
ord-a6775e3fb1694d95b4c4a0ae53ce811a
Source dataset
uspto-grants-1990_08
Patent number
US04952593

Reaction notes

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