Nitric Acid → HCID 86652704, compound

HRID 1258164Notes

Reaction equation

HRID 1258164 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>[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].[NH2:16][C:17]([NH2:4])=[NH:18]

Participants

6

Reactant 3

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

Product 1

HCID 86652704HCID 86652704, compoundYield 108.8%

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 (2) (98 g). Rf=0.1 (Methylene chloride:Methanol:25% Aqueous ammonia=150:10:1). MS: 195.2 (M+H); 1H-NMR (DMSO-d6)=1.43 (s, 3H), 6.59 (s, 3H), 6.72-6.76 (d, 1H), 7.21-7.27 (m, 1H), 8.63-8.64 (br, 1H).

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-2dbb689fbde24e55b8fd417a9d446442
Source dataset
uspto-grants-2013_06
Patent number
US08466154B2

Reaction notes

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