Water → N-hydroxy-2-(4-nitrophenyl)acetamidine

HRID 30662

Reaction equation

HRID 30662 reaction equation
Cl.[NH2:2][OH:3].CO.C[O-].[Na+].[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]#[N:20])=[CH:14][CH:13]=1)([O-])=[O:10].[OH2:21]>CS(C)=O>[OH:3][N:2]=[C:19]([NH2:20])[CH2:18][C:15]1[CH:14]=[CH:13][C:12]([N+:9]([O-:10])=[O:21])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 68386p-NitrophenylacetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 23694274Sodium methanolate methanol

Product 1

HCID 308292N-hydroxy-2-(4-nitrophenyl)acetamidineYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a mixture of hydroxylamine hydrochloride (21.5 g) and dimethyl sulfoxide (50 mL) was added dropwise 28% sodium methoxide methanol solution (59.6 g) at room temperature. A solution (50 mL) of (4-nitrophenyl)acetonitrile (10.0 g) in dimethyl sulfoxide was further added dropwise to the reaction mixture. The reaction mixture was stirred at 100° C. for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give N′-hydroxy-2-(4-nitrophenyl)ethanimidamide as brown crystals (7.10 g, yield 59%). Recrystallization thereof from ethyl acetate-diisopropyl ether gave brown prism crystals. melting point: 170-171° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-05d8c6aef45e47969bcddacab17cb55b
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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