Cyanamide → N,N'-dicyano-N"-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine

HRID 1702479Notes

Reaction equation

HRID 1702479 reaction equation
[Na].[N:2]#[C:3][NH2:4].[C:5]([NH:7][C:8](=[N:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][C:20]=1[CH3:21])SC)#[N:6]>C(O)C>[C:3]([NH:4][C:8]([NH:7][C:5]#[N:6])=[N:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][C:20]=1[CH3:21])#[N:2]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 1036301-Cyano-2-methyl-3-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)isothioureaHCID 5360545Sodium

Product 1

HCID 12918616N,N'-dicyano-N"-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidineYield 49.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium metal (1.01 g) in ethanol (120 ml) were added cyanamide (18.5 g) and N-cyano-S-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]isothiourea (10.76 g). The resulting mixture was heated under reflux for 1.5 hrs. After concentration under a reduced pressure, the residue was added to cold water (50 ml) and acidified (pH 4.5) with 10% HCl and cooled for 1 hr. in an ice bath. The precipitate was filtered, washed with water and dried. The resulting crude product (7.43 g) was recrystallized from C2H5OH-H2O (1:1) to give N,N'-dicyano-N"-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine (5.17 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 1.5 hrs
  3. concentrationAfter concentration under a reduced pressure
  4. additionthe residue was added to cold water (50 ml)
  5. temperaturecooled for 1 hr
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. customdried
  9. customThe resulting crude product (7.43 g) was recrystallized from C2H5OH-H2O (1:1)

Sources & evidence

ORD record
ord-c05a2444871f41fba6b7fac0cf1412bb
Source dataset
uspto-grants-1983_04
Patent number
US04381395

Reaction notes

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