Guanidine Hydrochloride → HCID 135546394, compound

HRID 1373009Notes

Reaction equation

HRID 1373009 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 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 standing to cool, the solvent was removed and to the residue was added tetrahydrofuran (500 mL). The insoluble matters were filtered off, and the filtrate was concentrated. To a solution of the residue in tetrahydrofuran (1500 mL) and methanol (100 mL) was added activated manganese dioxide (250 g), followed by heating under reflux. After 2 hours, additional activated manganese dioxide (100 g) was added and the mixture was heated under reflux further for one and a quarter hour. After standing to cool, manganese dioxide was filtered off through Celite, and washed with tetrahydrofuran and methanol. The combined filtrates were concentrated, and to the residue was added acetonitrile. 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. temperatureto cool
  4. customthe solvent was removed and to the residue
  5. additionwas added tetrahydrofuran (500 mL)
  6. filtrationThe insoluble matters were filtered off
  7. concentrationthe filtrate was concentrated
  8. additionTo a solution of the residue in tetrahydrofuran (1500 mL) and methanol (100 mL) was added activated manganese dioxide (250 g)
  9. temperatureby heating
  10. temperatureunder reflux
  11. additionadditional activated manganese dioxide (100 g) was added
  12. temperaturethe mixture was heated
  13. temperatureunder reflux further for one and a quarter hour
  14. temperatureto cool
  15. filtrationmanganese dioxide was filtered off through Celite
  16. washwashed with tetrahydrofuran and methanol
  17. concentrationThe combined filtrates were concentrated
  18. additionto the residue was added acetonitrile
  19. customThe resulting precipitates
  20. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e03fb2ab21714ca0b0690aec3718ee24
Source dataset
uspto-grants-2007_01
Patent number
US07160892B2

Reaction notes

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