Potassium Carbonate → N'-hydroxy-2-phenoxyethanimidamide

HRID 1159646

Reaction equation

HRID 1159646 reaction equation
[O:1]([CH2:8][C:9]#[N:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.[NH2:18][OH:19]>CCO.O>[OH:19][N:18]=[C:9]([NH2:10])[CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 241641PhenoxyacetonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2744271N'-hydroxy-2-phenoxyethanimidamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1 g of phenoxyacetonitrile, 2.4 g of K2CO3 and 1.2 g of hydroxylamine hydrochloride in 60 ml of EtOH and 10 ml of water is heated at reflux for 3 hours. The reaction mixture is concentrated under vacuum and the residue is taken up in water and extracted with AcOEt. The organic phase is extracted with 1N HCl solution, the aqueous phase is alkalified by adding 1N NaOH solution, extracted with AcOEt and dried over MgSO4, and the solvent is evaporated under vacuum. This gives 0.9 g of the expected compound in the form of a colourless oil which crystallizes.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture is concentrated under vacuum
  4. extractionextracted with AcOEt
  5. extractionThe organic phase is extracted with 1N HCl solution
  6. additionby adding 1N NaOH solution
  7. extractionextracted with AcOEt
  8. dry with materialdried over MgSO4
  9. customthe solvent is evaporated under vacuum
  10. customThis gives 0.9 g of the expected compound in the form of a colourless oil which crystallizes

Sources & evidence

ORD record
ord-7a741565db4d483abc8728eaaa00114c
Source dataset
uspto-grants-2010_10
Patent number
US07812165B2

Linked notes

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