Acetonitrile → N1-(4-methoxybenzyl)-cyanoguanidine

HRID 1437103Notes

Reaction equation

HRID 1437103 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.[N-:12]([C:15]#[N:16])C#N.[Na+].[C:18](#[N:20])C>>[CH3:2][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:9]([C:18]#[N:20])[C:15]([NH2:16])=[NH:12])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 27515821-(4-Methoxyphenyl)methanamine--hydrogen chloride (1/1)HCID 4350929Sodium dicyanamide

Product 1

HCID 23086859N1-(4-methoxybenzyl)-cyanoguanidine

Procedure

800 ml of acetonitrile was added to 70.0 g (0.40 mol) of 4-methoxybenzylamine hydrochloride and 39.5 g (0.44 mol) of sodium dicyanamide. The mixture was refluxed for 19 hours, and the solvent was distilled off under reduced pressure. The residue was heated and dissolved in methanol, and insolubles were filtered off. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate to obtain 67.0 g of colorless crystals having a melting point of 89 to 92° C.

Workup

  1. temperatureThe mixture was refluxed for 19 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. temperatureThe residue was heated
  4. dissolutiondissolved in methanol
  5. filtrationinsolubles were filtered off
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5c0bc9e639914480b38fef9cec2bc1ff
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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