Guanidine Hydrochloride → HCID 135546394, compound

HRID 747147Notes

Reaction equation

HRID 747147 reaction equation
[Na].[F:2][C:3]1[CH:4]=[C:5](/[CH:9]=[C:10](\[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)/[C:11](OCC)=[O:12])[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:23][C:24]([NH2:26])=[NH:25]>C(O)C>[NH2:25][C:24]1[NH:26][C:11](=[O:12])[C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=2)[N:23]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 57435649HCID 57435649, compound

Product 1

HCID 135546394HCID 135546394, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (3.4 g, 147 mmol) was dissolved in ethanol (500 ml), and then ethyl (E)-3-(3-fluorophenyl)-2-(4-pyridyl)-2-propenoate (33 g, 121 mmol) and guanidine hydrochloride (13.9 g, 146 mmol) were added thereto, followed by heating under reflux for 13 hours. After cooling as it was, the solvent was removed. Tetrahydrofuran (500 ml) was added to the residue, the insoluble matters were filtered off, and the filtrate was concentrated. To a solution of the residue in tetrahydrofuran (1500 ml)-methanol (100 ml) was added active manganese dioxide (250 g), followed by heating under reflux. After 2 hours, additional active manganese dioxide (100 g) was added thereto, followed by heating under reflux further for 1 hour and 15 minutes. After cooling as it was, the manganese dioxide was filtered off through Celite and washed with tetrahydrofuran and methanol. The collected filtrate was concentrated and acetonitrile was added to the residue. The resulting precipitates were collected by filtration, to give the title compound (15 g, 44%) as a yellow powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 13 hours
  3. temperatureAfter cooling as it
  4. customthe solvent was removed
  5. additionTetrahydrofuran (500 ml) was added to the residue
  6. filtrationthe insoluble matters were filtered off
  7. concentrationthe filtrate was concentrated
  8. additionTo a solution of the residue in tetrahydrofuran (1500 ml)-methanol (100 ml) was added active manganese dioxide (250 g)
  9. temperatureby heating
  10. temperatureunder reflux
  11. additionadditional active manganese dioxide (100 g) was added
  12. temperatureby heating
  13. temperatureunder reflux further for 1 hour and 15 minutes
  14. temperatureAfter cooling as it
  15. filtrationthe manganese dioxide was filtered off through Celite
  16. washwashed with tetrahydrofuran and methanol
  17. concentrationThe collected filtrate was concentrated
  18. additionacetonitrile was added to the residue
  19. customThe resulting precipitates
  20. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-b20abd8fb05b4cb98a949d46df898c28
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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