Cyanamide → 1-Benzylguanidine hydrochloride

HRID 1824018Notes

Reaction equation

HRID 1824018 reaction equation
[ClH:1].[CH2:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:10]#[C:11][NH2:12]>>[ClH:1].[CH2:2]([NH:9][C:11]([NH2:12])=[NH:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 9864CyanamideHCID 2724127Benzylammonium chloride

Product 1

HCID 1784794191-Benzylguanidine hydrochlorideYield 42.7%

Procedure

A mixture of benzylamine hydrochloride (4.3 g, 0.03 mol) and cyanamide (1.3 g, 0.031 mol) in xylenes (15 ml) was heated to reflux for 6 hours. After concentration, the reaction mixture was triturated with ether and the solid separated was filtered and crystallized from methanol to provide a colorless solid (2.38 g); purity: 96.8% (HPLC); 1H-NMR (CD3OD) δ 4.41 (s, 2H, CH2), 7.32–7.37 (m, 5H, Ar).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours
  3. concentrationAfter concentration
  4. customthe reaction mixture was triturated with ether
  5. customthe solid separated
  6. filtrationwas filtered
  7. customcrystallized from methanol

Sources & evidence

ORD record
ord-c53c08927df64ddda3e90a35e44c0e3f
Source dataset
uspto-grants-2006_05
Patent number
US07041702B1

Reaction notes

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