Hydrochloric Acid → N-Pentyl-N'-cyanoguanidine

HRID 280848Notes

Reaction equation

HRID 280848 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].Cl.[N-:8]([C:11]#[N:12])[C:9]#[N:10].[Na+]>CC(O)C>[CH2:1]([NH:6][C:11]([NH:8][C:9]#[N:10])=[NH:12])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8060PentylamineHCID 4350929Sodium dicyanamide

Product 1

HCID 178446444N-Pentyl-N'-cyanoguanidineYield 67.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Pentylamine (17.43 g, 0.20 mol) in 2-propanol (175 ml) was acidified with conc. HCl (17 ml, 0.204 mol) and then treated with sodium dicyanamide (23.15 g, 0.26 mol). The mixture was refluxed for 20 hours, allowed to cool and filtered through diatomaceous earth. The filtrate was concentrated in vacuo and the residue dissolved in chloroform. This solution was washed with water and dried over magnesium sulfate. Filtration and evaporation in vacuo gave 20.93 g (67.9%) of off-white solid; mass spec.: M+ at 154.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. temperatureto cool
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe residue dissolved in chloroform
  6. washThis solution was washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and evaporation in vacuo

Sources & evidence

ORD record
ord-d5205d72f94a4aebaf2f6ea2f74a59e2
Source dataset
uspto-grants-1986_05
Patent number
US04591595

Reaction notes

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