Potassium Carbonate → 4-chloro-N'-hydroxybenzenecarboximidamide

HRID 59258

Reaction equation

HRID 59258 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl.[OH:11][NH2:12].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[N:12][OH:11])[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 hydroxyl amine 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-32820b4765274f828d1aa5ef135e2b1d
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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