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

HRID 274751Notes

Reaction equation

HRID 274751 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-ca10e8df3bb149f4a29320d09ee7d05b
Source dataset
uspto-grants-1995_02
Patent number
US05389666

Reaction notes

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