Guanidine Hydrochloride → HCID 9921794, compound

HRID 457873Notes

Reaction equation

HRID 457873 reaction equation
[Na].[F:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:11]#[N:12])[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:20][C:21]([NH2:23])=[NH:22]>C(O)C>[F:2][C:3]1[CH:4]=[C:5]([C:9]2[N:20]=[C:21]([NH2:23])[N:22]=[C:11]([NH2:12])[C:10]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 670736703-(3-Fluorophenyl)-2-(4-pyridyl)-2-propene nitrile

Product 1

HCID 9921794HCID 9921794, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After sodium (6.2 g, 268 mmol) was dissolved in ethanol (700 mL), 3-(3-fluorophenyl)-2-(4-pyridyl)-2-propene nitrile (50 g, 223 mmol) and guanidine hydrochloride (25.6 g, 268 mmol) were added thereto in this order and heated under reflux for 4 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. A suspension of the residues and activated manganese dioxide (200 g) in chloroform (1000 mL) was heated under reflux for 2 hours. After cooling as it was, the manganese dioxide was filtered off through Celite, and washed with tetrahydrofuran (500 mL33 3) and methanol-chloroform (1:1) (1000 mL×2). The collected filtrate was concentrated, and then methanol was added to the residue. The resulting precipitates were collected by filtration, to give the title compound as a crude solid (14.6 g). The crude crystals were recrystallized from methanol-chloroform, to give the title compound (12.4 g, 20%) as a colorless solid.

Workup

  1. temperaturein this order and heated
  2. temperatureunder reflux for 4 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. additionA suspension of the residues and activated manganese dioxide (200 g) in chloroform (1000 mL)
  9. temperaturewas heated
  10. temperatureunder reflux for 2 hours
  11. temperatureAfter cooling as it
  12. filtrationthe manganese dioxide was filtered off through Celite
  13. washwashed with tetrahydrofuran (500 mL33 3) and methanol-chloroform (1:1) (1000 mL×2)
  14. concentrationThe collected filtrate was concentrated
  15. additionmethanol was added to the residue
  16. customThe resulting precipitates
  17. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7c735bc4e8484669be06a86309b0c52b
Source dataset
uspto-grants-2007_03
Patent number
US07189717B2

Reaction notes

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