Nitric Acid → HCID 178419082, compound

HRID 1373398Notes

Reaction equation

HRID 1373398 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].[N:14]#[C:15][NH2:16].[N+:17]([O-:20])([OH:19])=[O:18]>C(O)C>[N+:17]([O-:20])([O-:19])=[O:18].[CH3:13][O:12][C:8]1[CH:7]=[C:5]([NH:6][C:15]([NH2:16])=[NH2+:14])[CH:4]=[C:3]([O:2][CH3:1])[C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 9864CyanamideHCID 322853,4,5-Trimethoxyaniline

Product 1

HCID 178419082HCID 178419082, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a room temperature solution of 3,4,5-trimethoxyaniline (3.46 g, 18.9 mmol) in ethanol (20 mL) was added cyanamide (1.68 mL, 50 wt % in water, 21.7 mmol) followed by the dropwise addition of concentrated nitric acid (1.33 mL). The mixture was heated at reflux for 13 hours and allowed to cool to room temperature. The mixture was concentrated in vacuo to approximately 70% of its original volume and ether was added. The resulting precipitate was isolated on a filter to yield N-(3,4,5-trimethoxyphenyl)guanidinium nitrate (2.5 g, 46%) as a grey powder. 1H NMR (DMSO-d6): δ 9.47 (s, 1 H), 7.29 (s, 3 H), 6.57 (s, 2 H), 3.80 (s, 6 H), 3.68 (s, 3 H); 13C NMR (DMSO-d6): δ 155.78, 153.33, 136.07, 130.58, 102.90, 59.99, 55.96; MS m/z 226 (M+1 of free base).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 13 hours
  3. concentrationThe mixture was concentrated in vacuo to approximately 70% of its original volume and ether
  4. additionwas added
  5. customThe resulting precipitate was isolated on
  6. filtrationa filter

Sources & evidence

ORD record
ord-cccb3cf5eae84dc89c4dd4cf9b7f2dfb
Source dataset
uspto-grants-2007_01
Patent number
US07160897B2

Reaction notes

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