Phosphorus sulfide (P2S5) → HCID 14390444, compound

HRID 622981Notes

Reaction equation

HRID 622981 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH2:20])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>C(#N)C>[OH2:19].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18](=[S:22])[NH2:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 3082931Ahr 12245

Product 1

HCID 14390444HCID 14390444, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetamide (3.44 g, 0.012 mole) and phosphorus pentasulfide (1.47 g, 0.0033 mole) in 150 ml of dry acetonitrile (dried over molecular sieves) was heated at reflux for 3 hr. The reaction mixture was filtered and washed with boiling acetonitrile. The solid residue in the flask was treated with boiling methanol and filtered. The methanol and acetonitrile filtrates were combined and evaporated to dryness. The residue was treated with acetone and filtered through a silica gel filter funnel. The filtrate was treated with Florisil®, filtered, and evaporated to dryness. The residue was treated with acetone, applied to a silica gel column (7×15 cm), and eluted with acetone. The appropriate fractions were combined and evaporated. The residue was dissolved in hot methanol, treated with activated charcoal, and filtered through a Celite pad. The filtrate was concentrated to initiate crystallization. The mixture was diluted with water and ice, then filtered to collect the precipitate which was washed with water. The solid was dried under high vacuum overnight at room temperature, then at 55° C. for 5 hr. to give 0.31 g product (8.3%), mp 226°-29° C. with decomposition.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hr
  3. filtrationThe reaction mixture was filtered
  4. washwashed with boiling acetonitrile
  5. additionThe solid residue in the flask was treated with boiling methanol
  6. filtrationfiltered
  7. customevaporated to dryness
  8. additionThe residue was treated with acetone
  9. filtrationfiltered through a silica gel
  10. filtrationfilter funnel
  11. additionThe filtrate was treated with Florisil®
  12. filtrationfiltered
  13. customevaporated to dryness
  14. additionThe residue was treated with acetone
  15. washeluted with acetone
  16. customevaporated
  17. dissolutionThe residue was dissolved in hot methanol
  18. additiontreated with activated charcoal
  19. filtrationfiltered through a Celite pad
  20. concentrationThe filtrate was concentrated
  21. customcrystallization
  22. additionThe mixture was diluted with water and ice
  23. filtrationfiltered
  24. customto collect the precipitate which
  25. washwas washed with water
  26. customThe solid was dried under high vacuum overnight at room temperature

Sources & evidence

ORD record
ord-9bb0149e9764466481c02ab2298bafd3
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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