Potassium Carbonate → 2-(4-chlorophenyl)-N'-hydroxyethanimidamide

HRID 1023160Notes

Reaction equation

HRID 1023160 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Cl.[NH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[N:12][OH:13])[NH2:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2415824-Chlorobenzyl cyanideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2493452-(4-chlorophenyl)-N'-hydroxyethanimidamideYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-(4-chlorophenyl)acetonitrile (1 g, 6.5 mmol) in ethanol (20 mL) at room temperature, hydroxylamine hydrochloride (4.5 g, 65.6 mmol) and potassium carbonate (12.5 g, 91 mmol) were added and heated at 80° C. overnight. Solvent was removed under vacuum. The residue was dissolved in ethyl acetate (50 mL) and the solution was washed with water and brine, and dried over sodium sulfate. Solvent was removed under vacuum to afford 2-(4-chlorophenyl)-N′-hydroxyacetimidamide (1 g, 83%) as an off-white solid. 1H NMR: 400 MHZ, DMSO-d6: δ 3.26 (s, 2H), 5.43 (s, 2H), 7.29-7.30 (m, 2H), 7.34-7.34 (m, 2H), 8.91 (s, 1H). LCMS: RT 0.89 min. LCMS (ES-API), m/z 186.0 (M+H).

Workup

  1. customSolvent was removed under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  3. washthe solution was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-cfc09dea4cc345839bea271add43055a
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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