Hydrochloric Acid → Carbonic acid, compound with phenylguanidine (1:1)

HRID 1197679Notes

Reaction equation

HRID 1197679 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N:9]#[C:10][NH2:11].[C:12](=[O:15])([O-:14])[OH:13].[Na+]>O>[C:12](=[O:13])([OH:15])[OH:14].[C:2]1([NH:1][C:10]([NH2:11])=[NH:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 6115AnilineHCID 9864Cyanamide2×HCID 516892Sodium Bicarbonate

Product 1

HCID 16217093Carbonic acid, compound with phenylguanidine (1:1)Yield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
87 °C

Procedure

To 98.2 g aniline (1.0 mol) is added 32% HCl until the pH of the solution reaches approximately 2.5; 95.2 g (0.83 mol) 32% HCl are required. The solution is heated to 87° C. and stirred while 93.0 g of a 50% aqueous solution of cyanamide (1.10 mol) are added over a period of 1 hour. Shortly before completion of the cyanamide addition, another 16.8 g (0.15 mol) 32% HCl are added. After 3 hours stirring at 87° C. the solution is cooled to 60° C. and added to a stirred suspension of 101.0 g (1.20 mol) sodium hydrogencarbonate in 170 ml water at 60° C. After cooling to 5° C., 127.6 g phenylguanidine hydrogencarbonate (dried at 45° C./100 mbar) are isolated (66.8% free base), representing a yield of 94.5% based on aniline. The melting point (decomposition) is 150° to 152° C.

Workup

  1. additionare added over a period of 1 hour
  2. temperatureis cooled to 60° C.
  3. temperatureAfter cooling to 5° C.

Sources & evidence

ORD record
ord-6c3fbc34eb91424eaf3b2e4cf6c415fc
Source dataset
uspto-grants-1994_01
Patent number
US05276186

Reaction notes

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