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

HRID 1197678Notes

Reaction equation

HRID 1197678 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:9]#[C:10][NH2:11].[C:12](=[O:15])([O-:14])[O-:13].[Na+].[Na+]>O>[C:12](=[O:13])([OH:15])[OH:14].[C:3]1([NH:2][C:10]([NH2:11])=[NH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6115AnilineHCID 9864Cyanamide2×HCID 10340Sodium Carbonate

Product 1

HCID 16217093Carbonic acid, compound with phenylguanidine (1:1)Yield 92.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

88.5 g (0.78 mol) aqueous HCl (32% by weight) are added to 93.1 g aniline (1.0 mol) until the pH value reaches 2.0. Over the course of 1 hour, 92.4 g (1.1 mol) of a 50% aqueous cyanamide solution are run into the reaction mixture at 85° C. Towards the end of the cyanamide addition, a further 22.1 g (0.19 mol) aqueous HCl (32%) are added, which returns the pH to 2.4 to 2.7. After stirring for 2 hours at 85° C., the mixture is allowed to cool to 60° C. and a solution of 63.6 g (0.6 mol) sodium carbonate in 170 ml water is added over a 30 minute period. The crystalline precipitate is filtered after cooling to 5° C. 163 g phenylguanidine carbonate are produced, containing 76.7% phenylguanidine free base, which corresponds to a 92.7% yield based on aniline. The melting point (decomposition) is 147° to 150° C.

Workup

  1. customare run into the reaction mixture at 85° C
  2. temperatureto cool to 60° C.
  3. filtrationThe crystalline precipitate is filtered
  4. temperatureafter cooling to 5° C

Sources & evidence

ORD record
ord-be75fe1d78cc4efbbfa7d6f5b517100e
Source dataset
uspto-grants-1994_01
Patent number
US05276186

Reaction notes

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