Nitric Acid → HCID 178512503, compound

HRID 47196Notes

Reaction equation

HRID 47196 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N+:9]([O-:12])([OH:11])=[O:10].[N:13]#[C:14][NH2:15]>CCO>[N+:9]([O-:12])([OH:11])=[O:10].[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14]([NH2:15])=[NH:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 78124-ChloroanilineHCID 9864Cyanamide

Product 1

HCID 178512503HCID 178512503, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloroaniline (70 mmol, 8.88 g) in EtOH (5 mL) on an ice bath was treated with nitric acid (69% aq soln.; 5 mL). To this mixture cyanamide (50% aq. soln.; 5.4 mL) was added. The reaction mixture was stirred at r.t. for 10 min and then refluxed under N2 for a further 22 h. The solvent was evaporated. The dark brown solid residue was washed with EtOH and was dried under high vacuum to afford the title compound as a white powder (7.16 g, 44%). 1H-NMR (300 MHz, d6-DMSO) δ7.27-7.54 (m, 4H, Ph-H), 9.65 (br. s, 2H, NH).

Workup

  1. temperaturerefluxed under N2 for a further 22 h
  2. customThe solvent was evaporated
  3. washThe dark brown solid residue was washed with EtOH
  4. customwas dried under high vacuum

Sources & evidence

ORD record
ord-0f54e6ba105d4bdfbd6b305845f9179c
Source dataset
uspto-grants-2004_03
Patent number
US06699854B2

Reaction notes

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