Nitric Acid → 3-Nitrophenylguanidine Nitrate

HRID 440865Notes

Reaction equation

HRID 440865 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[N+:5]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])([O-:7])=[O:6].[N:15]#[C:16][NH2:17]>C(O)C>[N+:1]([O-:4])([OH:3])=[O:2].[N+:5]([C:8]1[CH:9]=[C:10]([NH:11][C:16]([NH2:17])=[NH:15])[CH:12]=[CH:13][CH:14]=1)([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 74233-NitroanilineHCID 9864Cyanamide

Product 1

HCID 1785125133-Nitrophenylguanidine Nitrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

42 ml (0.6 mol) of nitric acid (65%) are added dropwise to a yellow suspension of 82.88 g (0.6 mol) of 3-nitroaniline in 200 ml of ethanol. After the exothermic reaction has subsided, 75.7 g (0.9 mol) of cyanamide (50% in water) are added and the reaction mixture is boiled at reflux for 21 hours. After cooling to 0°, the mixture is filtered and washed six times with ethanol/diethyl ether (1:1). Drying under HV at 40° yields 3-nitrophenyl-guanidine nitrate; m.p. 205°-207°.

Workup

  1. customAfter the exothermic reaction
  2. temperatureat reflux for 21 hours
  3. temperatureAfter cooling to 0°
  4. filtrationthe mixture is filtered
  5. washwashed six times with ethanol/diethyl ether (1:1)
  6. customDrying under HV at 40°

Sources & evidence

ORD record
ord-cf70fac212664ab88b8c2c961aaf89c2
Source dataset
uspto-grants-1996_05
Patent number
US05521184

Reaction notes

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