Guanidine → HCID 178513105, compound

HRID 1154010Notes

Reaction equation

HRID 1154010 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[OH-].[Na+].NC(N)=N.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:19]([O:26][C:27]1[C:28]([Cl:37])=[C:29]([N:34]=[C:35]=[O:36])[C:30]([Cl:33])=[CH:31][CH:32]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:26][C:27]1[C:28]([Cl:37])=[C:29]([NH:34][C:35]([NH:4][C:3](=[NH:5])[NH2:2])=[O:36])[C:30]([Cl:33])=[CH:31][CH:32]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 3520GuanidineHCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 13369979HCID 13369979, compound

Product 1

HCID 178513105HCID 178513105, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Guanidine hydrochloride (7.8 g) is suspended in acetone (150 ml). A 50% aqueous sodium hydroxide solution (6.53 g) is added to the guanidine suspension. The mixture is stirred for one and one-half hours, after which 15 g anhydrous sodium sulfate are added and the reaction mixture stirred vigorously for an additional hour. The isocyanate obtained in Step 5 above (8.0 g) is dissolved and suspended in 50 ml acetone. This suspension is added to the reaction mixture over a period of one hour fifteen minutes. The reaction mixture is stirred overnight, filtered, and the filtrate evaporated in vacuo to a green oil. The green oil is triturated in 200 ml of H2O containing 5 drops of a 50% aqueous sodium hydroxide solution. The resulting suspension is stirred for three hours, filtered, and the solid washed with water and dried. After air drying overnight, there is obtained 12.9 g of a white powder which is dried in vacuo at 30°-35° C. for four hours, giving 9.47 g of white powder. The powder is dissolved in 50 ml of methanol. The methanol solution is filtered and the filtrate acidified with methanol/HCl. The acidified solution is evaporated in vacuo (30°-35° C.) to yield the hydrochloride salt as a light-colored oil, which is utilized without further treatment.

Workup

  1. stirringthe reaction mixture stirred vigorously for an additional hour
  2. additionThis suspension is added to the reaction mixture over a period of one hour fifteen minutes
  3. stirringThe reaction mixture is stirred overnight
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo to a green oil
  6. customThe green oil is triturated in 200 ml of H2O containing 5 drops of a 50% aqueous sodium hydroxide solution
  7. stirringThe resulting suspension is stirred for three hours
  8. filtrationfiltered
  9. washthe solid washed with water
  10. customdried
  11. customAfter air drying overnight

Sources & evidence

ORD record
ord-e0c5d84f6f374fbea1af4dfc6d1cb79e
Source dataset
uspto-grants-1984_12
Patent number
US04487779

Reaction notes

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