Thiophenol → HCID 20262908, compound

HRID 464312Notes

Reaction equation

HRID 464312 reaction equation
[ClH:1].O=[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]1[C:9]([O:11]C)=O.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>O>[ClH:1].[CH2:5]1[C:4]2[C:9](=[O:11])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:19][C:3]=2[CH2:8][CH2:7][NH:6]1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 516892Sodium BicarbonateHCID 70478900HCID 70478900, compound

Product 1

HCID 20262908HCID 20262908, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2.33 g of methyl 4-oxo-3-pyridinecarboxylate hydrochloride and 1.1 ml of thiophenol were slowly added at 100° C. with stirring to 35 g of polyphosphoric acid and the mixture was stirred at 100° C. for 4 hours and was then poured into 500 ml of water. The pH of the mixture was adjusted to 8 by addition of sodium bicarbonate and the mixture was extracted with chloroform three times. The organic phase was washed with water, dried over magnesium sulfate and filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was dissolved in a small amount of chloroform and the solution was acidified with a solution of hydrogen chloride in ether. Additional ether was added and the mixture was filtered. The product was crystallized from aqueous methanol and dried over P2O5 to obtain 1.365 g (54% yield) of 1,2,3,4-tetrahydro-10H-(1)-benzothiopyrano[3,2-c]pyridin-10-one hydrochloride melting at 270°-272° C. (decomp.)

Workup

  1. extractionthe mixture was extracted with chloroform three times
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate was evaporated to dryness under reduced pressure
  6. dissolutionThe residue was dissolved in a small amount of chloroform
  7. additionAdditional ether was added
  8. filtrationthe mixture was filtered
  9. customThe product was crystallized from aqueous methanol
  10. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-59b2cdb5a34a489a80d29cf331e2f95c
Source dataset
uspto-grants-1985_10
Patent number
US04547507

Reaction notes

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