Nitric Acid → HCID 178418691, compound

HRID 1725585Notes

Reaction equation

HRID 1725585 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]#[C:9][NH2:10].[N+:11]([O-:14])([OH:13])=[O:12].C(OCC)C>C(O)C>[N+:11]([O-:14])([OH:13])=[O:12].[C:2]1([NH:1][C:9]([NH2:10])=[NH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 6115AnilineHCID 9864Cyanamide

Product 1

HCID 178418691HCID 178418691, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of aniline (1.28 ml, 14 mmol) in ethanol (14 ml) was added cyanamide (1.25 ml, 16.1 mmol) and nitric acid (1 ml, 14 mmol), and the reaction was heated to reflux. After 16 hours, the reaction was cooled to room temperature and poured into diethyl ether. The resulting precipitate was filtered and dried to afford the title compound as a gray solid (2.50 g, 13 mmol, 90%). NMR (300 MHz, CD3OD): δ 7.47 (m, 2H), 7.36 (m, 1H), 7.30 (m, 2H).

Workup

  1. temperaturethe reaction was heated to reflux
  2. filtrationThe resulting precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-64ae573d4cef4f60870ff79720e3a850
Source dataset
uspto-grants-2009_02
Patent number
US07491731B2

Reaction notes

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