Nitric Acid → HCID 178426527, compound

HRID 736301Notes

Reaction equation

HRID 736301 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[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:5]([NH:6][C:17]([NH2:18])=[NH:16])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 83904-Methyl-3-nitroanilineHCID 9864Cyanamide

Product 1

HCID 178426527HCID 178426527, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-Methyl-3-nitroaniline (90 g, 0.592 mol) was dissolved in ethanol (250 ml) and 65% aqueous nitric acid solution (59 g, 0.592 mol) was added thereto. When the exothermic reaction is stopped, cyanamide (74.6 g) dissolved in water in a concentration of 50% was added. The brown mixture was reacted under reflux for 24 hours. The reaction mixture was cooled to 0° C., filtered, and washed with diethylether to give 4-methyl-3-nitrophenyl-guanidine nitrate (93 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 diethylether

Sources & evidence

ORD record
ord-2401db9e1dfd4cb0b1135d1633b53fdb
Source dataset
uspto-grants-2009_09
Patent number
US07595323B2

Reaction notes

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