Sodium Carbonate → HCID 178513348, compound

HRID 1665617Notes

Reaction equation

HRID 1665617 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]>C(O)C.O>[OH:3][NH:2][C:17](=[NH:18])[C:16]1[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 120904-NitrobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178513348HCID 178513348, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Hydroxylamine hydrochloride (1.9 g, 27.2 mmol) then sodium carbonate (2.2 g, 20.4 mmol) were added to a stirred solution of 4-nitro-benzonitrile (1 g, 6.8 mmol) in ethanol (20 mL) and water (8 mL). The resulting mixture was refluxed at 85° C. under an atmosphere of nitrogen for 2 hours. The volatiles were then evaporated and the residue was extracted with ethyl acetate. The organics were washed with brine solution, dried over Na2SO4 and evaporated to afford 1.2 g (98%) of N-hydroxy-4-nitro-benzamidine. 1H NMR: (DMSO-d6): δ 10.2 (s, 1H), 8.24 (d, 2H), 7.97 (d, 2H), 6.03 (s, 2H).

Workup

  1. customThe volatiles were then evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organics were washed with brine solution
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-4a973373971742dfb3acef45c344af24
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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