Benzamidine, hydrochloride → HCID 68452419, compound

HRID 2354470Notes

Reaction equation

HRID 2354470 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[O-].[Na+].Br[CH:15]([CH3:28])[C:16]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)=O>O1CCCC1>[C:3]1([C:2]2[NH:9][C:15]([CH3:28])=[C:16]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=3)[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 10942334Sodium Methoxide2×HCID 125874062-Bromo-1-(naphthalen-2-yl)propan-1-one

Product 1

HCID 68452419HCID 68452419, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Benzamidine hydrochloride and an equimolar amount of sodium methylate were heated under reflux in tetrahydrofuran for 1 hour. After cooling, a tetrahydrofuran solution of an equimolar amount of 2-bromo-2′-propionaphthone was added dropwise thereto so that the temperature did not exceed 30° C., and then an equimolar amount of sodium methylate was further added, followed by heating under reflux for 1 hour. After removal of the solvent by distillation under reduced pressure, the residue was washed with water and subjected to recrystallization from acetonitrile to obtain grayish blue crystals.

Workup

  1. temperatureAfter cooling
  2. customdid not exceed 30° C.
  3. temperatureby heating
  4. temperatureunder reflux for 1 hour
  5. customAfter removal of the solvent
  6. distillationby distillation under reduced pressure
  7. washthe residue was washed with water
  8. customsubjected to recrystallization from acetonitrile
  9. customto obtain grayish blue crystals

Sources & evidence

ORD record
ord-2441b9b82fae4edba2713fff78b26118
Source dataset
uspto-grants-2010_07
Patent number
US07754105B2

Reaction notes

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