Sodium Hydroxide → 2-(2-Ethyl [1,3]dioxolan-2-yl)-N-hydroxy-acetamidine

HRID 1182115Notes

Reaction equation

HRID 1182115 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[CH2:6]([C:8]1([CH2:13][C:14]#[N:15])[O:12][CH2:11][CH2:10][O:9]1)[CH3:7]>O.CO>[CH2:6]([C:8]1([CH2:13][C:14]([NH:4][OH:1])=[NH:15])[O:12][CH2:11][CH2:10][O:9]1)[CH3:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 69357458(2-Ethyl-[1,3]dioxolan-2-yl)-acetonitrile

Product 1

HCID 1784368352-(2-Ethyl [1,3]dioxolan-2-yl)-N-hydroxy-acetamidine

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of NaOH (1.17 g, 29.3 mmol) in water/methanol (1:1) (18 ml), cooled to 0° C. in an ice bath, is treated with hydroxylamine hydrochloride (1.58 g, 22.78 mmol), with stirring for 5 minutes. (2-Ethyl-[1,3]dioxolan-2-yl)-acetonitrile (1.42 g, 10.125 mmol) is added and the reaction mixture stirred at room temperature for 18 hours, then refluxed for a further 2 hours. The reaction mixture is cooled and partitioned between ethyl acetate and water. The organic phase is dried over MgSO4, filtered, and the solvent evaporated to yield 2-(2-Ethyl [1,3]dioxolan-2-yl)-N-hydroxy-acetamidine. [M+H] 175.21

Workup

  1. stirringthe reaction mixture stirred at room temperature for 18 hours
  2. temperaturerefluxed for a further 2 hours
  3. temperatureThe reaction mixture is cooled
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-4059495ffebc446bbaf2a7eb39ac22a3
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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