Water → Ethyl 4-nitrophenoxyethaneimidoate

HRID 404857

Reaction equation

HRID 404857 reaction equation
[OH-:1].[K+].O[N:4]=[C:5]([O:7][CH2:8][CH3:9])[CH3:6].Cl[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.O>CN(C)C=O>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([O:1][CH2:6][C:5](=[NH:4])[O:7][CH2:8][CH3:9])=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 74741-Chloro-4-nitrobenzene2×HCID 14797Potassium HydroxideHCID 99894Ethyl acetohydroximate2×

Product 1

HCID 9991187Ethyl 4-nitrophenoxyethaneimidoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of 23.8 g (0.42 mol) of potassium hydroxide in 220 ml of N,N-dimethylformamide at 10° C. are added 40.0 g of ethyl N-hydroxyethaneimidoate (0.39 mol) (compound VI: R3═C2H5; R4═CH3). A solution of 55.6 g of 4-chloronitrobenzene (0.35 mol) (compound V: Hal=Cl) (55.6 g) in N,N-dimethylformamide is then added slowly, at 10° C. The mixture is stirred for 24 hours at 20° C. and 1 L of water is then added. The precipitate is filtered off and the solid is washed with water and oven-dried at 30° C. under vacuum to constant weight.

Workup

  1. filtrationThe precipitate is filtered off
  2. washthe solid is washed with water
  3. customoven-dried at 30° C. under vacuum to constant weight

Sources & evidence

ORD record
ord-d46f5127637a48c9b07b7e6c23bfa1f8
Source dataset
uspto-grants-2014_06
Patent number
US08748636B2

Linked notes

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