Nitric Acid → HCID 178426711, compound

HRID 2195719Notes

Reaction equation

HRID 2195719 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].[N+:12]([O-:15])([OH:14])=[O:13].[N:16]#[C:17][NH2:18].O>C(O)CCC>[N+:12]([O-:15])([OH:14])=[O:13].[CH3:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[NH:1][C:17]([NH2:18])=[NH:16]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 74442-Methyl-5-NitroanilineHCID 9864Cyanamide

Product 1

HCID 178426711HCID 178426711, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

To 2-amino-4-nitro toluene 1 (0.033 mol) in n-butanol (29 mL) is added nitric acid (2.1 g, 65% in water) followed by cyanamide solution in water (2 mL, 0.047 mmol). The resulting mixture is heated at reflux for 25 h. After cooling to 0° C., filtration and washing with 1:1=ethanol:diethyl ether (30 mL), 2-methyl-5-nitrophenyl guanidine nitrate 2 is obtained. To 2-methyl-5-nitrophenyl guanidine 2 (0.0074 mol) in isopropanol (15 ME) is added 3 (0.0074 mol) and sodium hydroxide flakes (0.008 mol). The resulting mixture is heated at reflux for 12 h. After cooling to 0° C., the product is collected by filtration and washed with isopropanol (6 mL) and methanol (3 mL) to afford 4. 1H NMR (400 MHz, d6-DMSO) δ 9.31 (s, 1H), 9.24 (s, 1H), 8.78 (m, 1H), 8.70 (m, 1H), 8.61 (m, 1H), 8.47 (m, 1H), 7.88 (m, 1H), 7.55 (m, 3H), 2.39 (s, 3H). MS (m/z) (M+1)+: 278.2.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 25 h
  3. filtrationfiltration
  4. washwashing with 1:1=ethanol

Sources & evidence

ORD record
ord-c7b9cca1073f435da81ebc246646148f
Source dataset
uspto-grants-2012_12
Patent number
US08338417B2

Reaction notes

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