Potassium Carbonate → 4-chloro-N'-hydroxybenzenecarboximidamide

HRID 508747Notes

Reaction equation

HRID 508747 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl.[NH2:11][OH:12].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[N:11][OH:12])[NH2:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 121634-ChlorobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2246504-chloro-N'-hydroxybenzenecarboximidamideYield 40.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-chloro benzonitrile (1.000 g, 7.26 mmol) in ethanol (20 mL) was added hydroxylamine HCl (0.752 g, 10.90 mmol) and potassium carbonate (3.00 g, 21.80 mmol). The reaction mass was refluxed for 10-12 h. Excess of solvent was removed under vacuum and the residue was diluted with water, acidified with dilute HCl. Precipitate obtained was filtered off and sucked dried to afford 0.500 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 5.88 (br s, 2H), 7.42 (d, J=8.1 Hz, 2H), 7.68 (d, J=8.4 Hz, 2H), 9.70 (br s, 1H); MS (m/z): 171.13 (M+H)+.

Workup

  1. temperatureThe reaction mass was refluxed for 10-12 h
  2. customExcess of solvent was removed under vacuum
  3. additionthe residue was diluted with water
  4. customPrecipitate obtained
  5. filtrationwas filtered off
  6. customsucked dried

Sources & evidence

ORD record
ord-5e0499b2367e4ad8a9e275548b961804
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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