Diphenylacetonitrile → N'-hydroxy-2,2-diphenylethanimidamide

HRID 1737198Notes

Reaction equation

HRID 1737198 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)C.O>[C:10]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[N:17][OH:18])[NH2:9])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6837DiphenylacetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 2913048N'-hydroxy-2,2-diphenylethanimidamideYield 30.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of diphenylacetonitrile (7.0 g), hydroxylamine hydrochloride (3.03 g), and sodium acetate (6.67 g) in 150 ml of 5:1 ethanol-water was refluxed for 4 h. The mixture was concentrated under reduced pressure. The residue was triturated with water, filtrated, and dried to give the title compound (2.5 g) having the following physical data.

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was triturated with water
  4. filtrationfiltrated
  5. customdried

Sources & evidence

ORD record
ord-41824d6f5ec6421e8623de9f9f91cb1f
Source dataset
uspto-grants-1999_10
Patent number
US05962439

Reaction notes

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