4-Ethenylbenzonitrile → N-Hydroxy-4-vinyl-benzamidine

HRID 1948514Notes

Reaction equation

HRID 1948514 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[CH2:2].Cl.[NH2:12][OH:13].C(=O)(O)[O-].[Na+]>CC(O)C.C(OCC)(=O)C>[OH:13][N:12]=[C:7]([NH2:8])[C:6]1[CH:9]=[CH:10][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 769674-EthenylbenzonitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 74440816N-Hydroxy-4-vinyl-benzamidineYield 96.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-vinylbenzonitrile (4.36 g, 33.8 mmol) and hydroxylamine hydrochloride (4.69 g, 67.5 mmol) in 2-propanol (50 mL) was added sodium bicarbonate (11.34 g, 135 mmol). The reaction mixture was heated at 80° C. for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried MgSO4, filtered, and concentrated to yield 5.3 g of N′-hydroxy-4-vinylbenzimidamide. MS (m+1)=163. HPLC Peak RT=0.53 minutes (Analytical Method B).

Workup

  1. washwashed with water
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9cd4ae3661cf457e8a0ec17500c06b94
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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