3-Hydroxypyridine → HCID 21329995, compound

HRID 614062Notes

Reaction equation

HRID 614062 reaction equation
Cl[C:2]1[C:7](=[O:8])[C:6]([Cl:9])=[N:5][S:4][N:3]=1.[OH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C(N(CC)CC)C>O1CCCC1>[Cl:9][C:6]1[C:7](=[O:8])[C:2]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:3][S:4][N:5]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 8471TriethylamineHCID 3540263,5-Dichloro-4H-1,2,6-thiadiazin-4-one

Product 1

HCID 21329995HCID 21329995, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 12.8 grams (0.07 mole) of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one and 6.7 grams (0.07 mole) of 3-hydroxypyridine in 300 ml of tetrahydrofuran was added dropwise 7.1 grams (0.07 mole) of triethylamine. During the addition the exothermic reaction caused the reaction mixture temperature to rise to 34° C. Upon complete addition, the reaction mixture was stirred for 16 hours during which time it cooled to ambient temperature. The reaction mixture was filtered to remove triethylamine hydrochloride. The filter cake was washed with tetrahydrofuran. The filtrate and wash were combined and evaporated under reduced pressure to a residual solid. The residue was triturated with 300 ml of distilled water and the insolubles collected by filtration. The filter cake was washed with water and recrystallized twice from ethanol. A sample of the recrystallized solid was dissolved in chloroform and subjected to analysis by thin layer chromatography. This analysis indicated that the solid contained impurities. The filtrates from the recrystallizations were combined and evaporated under reduced pressure to a residue. The residue was combined with the twice-recrystallized solid and dissolved in chloroform. The solution was slurried with silica gel in an effort to remove the impurities. The mixture was filtered and the filtrate was evaporated under reduced pressure to a residual solid. The solid was recrystallized from ethanol to give 7.0 grams (42%) of 3-chloro-5-(3-pyridyloxy)-4H-1,2,6-thiadiazin-4-one; m.p. 134.5°-135.5° C.

Workup

  1. additionDuring the addition
  2. customthe exothermic reaction
  3. customto rise to 34° C
  4. additionUpon complete addition
  5. filtrationThe reaction mixture was filtered
  6. customto remove triethylamine hydrochloride
  7. washThe filter cake was washed with tetrahydrofuran
  8. washThe filtrate and wash
  9. customevaporated under reduced pressure to a residual solid
  10. distillationThe residue was triturated with 300 ml of distilled water
  11. filtrationthe insolubles collected by filtration
  12. washThe filter cake was washed with water
  13. customrecrystallized twice from ethanol
  14. dissolutionA sample of the recrystallized solid was dissolved in chloroform
  15. customThe filtrates from the recrystallizations
  16. customevaporated under reduced pressure to a residue
  17. dissolutiondissolved in chloroform
  18. customto remove the impurities
  19. filtrationThe mixture was filtered
  20. customthe filtrate was evaporated under reduced pressure to a residual solid
  21. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-c51a04c7dce64385bdbdc627fde139d5
Source dataset
uspto-grants-1979_03
Patent number
US04143138

Reaction notes

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