Ethanol → 5-[4-(4-Oxo-1,4-dihydropyridin-1-yl)phenyl]-1,3,4-thiadiazol-2(3H)-one

HRID 5804Notes

Reaction equation

HRID 5804 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12](=[O:14])[NH:11][N:10]=2)=[CH:5][CH:4]=1.O1[CH:20]=[CH:19][C:18](=[O:21])[CH:17]=[CH:16]1.C(O)C>O>[O:21]=[C:18]1[CH:19]=[CH:20][N:2]([C:3]2[CH:4]=[CH:5][C:6]([C:9]3[S:13][C:12](=[O:14])[NH:11][N:10]=3)=[CH:7][CH:8]=2)[CH:16]=[CH:17]1

Participants

5

Reactant 3

HCID 702EthanolHCID 79684H-pyran-4-oneHCID 19794230HCID 19794230, compound

Product 1

HCID 197942275-[4-(4-Oxo-1,4-dihydropyridin-1-yl)phenyl]-1,3,4-thiadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(4-aminophenyl)-1,3,4-thiadiazol-2(3H)-one hydrochloride (1.25 g), 4H-pyran-4-one (0.58 g), ethanol (10 ml) and water (50 ml) was stirred under reflux under nitrogen for 31/2 hours. The cooled reaction mixture was filtered and the collected orange solid was washed with aqueous potassium hydrogen carbonate and water and was dried. The crude product (1.35 g) was treated with boiling dimethylformamide (200 ml) and the resultant suspension was cooled and filtered. The collected solid was washed with ethanol and ether, dried and suspended in water (100 ml). Sufficient aqueous sodium hydroxide (2N) was added to the suspension to form a solution which was filtered. The filtrate was acidified to pH 6 with hydrochloric acid which caused the precipitation of the title compound as a yellow solid, 0.96 g, m.p. 343°-4° C. (decomp).

Workup

  1. temperatureunder reflux under nitrogen for 31/2 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. washthe collected orange solid was washed with aqueous potassium hydrogen carbonate and water
  5. customwas dried
  6. additionThe crude product (1.35 g) was treated with boiling dimethylformamide (200 ml)
  7. temperaturethe resultant suspension was cooled
  8. filtrationfiltered
  9. washThe collected solid was washed with ethanol and ether
  10. customdried
  11. additionSufficient aqueous sodium hydroxide (2N) was added to the suspension
  12. customto form a solution which
  13. filtrationwas filtered
  14. customthe precipitation of the title compound as a yellow solid, 0.96 g, m.p. 343°-4° C. (decomp)

Sources & evidence

ORD record
ord-5b3edb5c38374dab95408851f226d3f9
Source dataset
uspto-grants-1993_09
Patent number
US05246928

Reaction notes

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