Nitric Acid → HCID 178426711, compound

HRID 736293Notes

Reaction equation

HRID 736293 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[N+:12]([O-:15])([OH:14])=[O:13].[N:16]#[C:17][NH2:18]>C(O)C.O>[N+:12]([O-:15])([OH:14])=[O:13].[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH:4][C:17]([NH2:18])=[NH:16]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 74442-Methyl-5-NitroanilineHCID 9864Cyanamide

Product 1

HCID 178426711HCID 178426711, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-5-nitroaniline (100 g, 0.657 mol) was dissolved in ethanol (250 ml), and 65% aqueous nitric acid solution (48 ml, 0.65 mol) was added thereto. When the exothermic reaction was stopped, cyanamide (41.4 g) dissolved in water (41.4 g) was added thereto. The brown mixture was reacted under reflux for 24 hours. The reaction mixture was cooled to 0° C., filtered, and washed with ethanol:diethyl ether (1:1, v/v) to give 2-methyl-5-nitrophenyl-guanidine nitrate (98 g).

Workup

  1. customWhen the exothermic reaction
  2. additionwas added
  3. customThe brown mixture was reacted
  4. temperatureunder reflux for 24 hours
  5. filtrationfiltered
  6. washwashed with ethanol:diethyl ether (1:1

Sources & evidence

ORD record
ord-4fd3f2bd76ad48eca9a738603783d2e5
Source dataset
uspto-grants-2009_09
Patent number
US07595323B2

Reaction notes

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