Water → Ethyl N-(4-nitrophenoxy)ethanimidate

HRID 1625193Notes

Reaction equation

HRID 1625193 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH:11][N:12]=[C:13]([O:15][CH2:16][CH3:17])[CH3:14].[OH-].[Na+].O>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:11][N:12]=[C:13]([O:15][CH2:16][CH3:17])[CH3:14])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 74741-Chloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 99894Ethyl acetohydroximate

Product 1

HCID 71416420Ethyl N-(4-nitrophenoxy)ethanimidateYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
17 °C

Procedure

4-Chloronitrobenzene, 136.2 g, and 111.4 g ethyl N-hydroxyacetimidate are dissolved in 216 ml DMF. The temperature is adjusted to 30° C. and 41.6 g solid NaOH is added in 8 portions keeping the temperature at 30-35° C. After one hour the temperature is adjusted to 40-45° C. and the mixture stirred for 1.5 hours. Cooling is applied and 520 ml water is fed at such a rate as to keep the temperature at ca 40° C. The slurry formed is cooled to 17° C. and filtered. The filter cake is washed with 175 ml ethanol/water 90/10 (V/V) followed by 175 ml water. Wet product, 214.5 g, corresponding to 192 g dry ethyl N-(4-nitrophenoxy)acetimidate is isolated. Yield 98.5%.

Workup

  1. customis adjusted to 30° C.
  2. customat 30-35° C
  3. temperatureCooling
  4. customat ca 40° C
  5. customThe slurry formed
  6. filtrationfiltered
  7. washThe filter cake is washed with 175 ml ethanol/water 90/10 (V/V)

Sources & evidence

ORD record
ord-d09126372a5e42b48a9da1a48c94d999
Source dataset
uspto-grants-2014_07
Patent number
US08779201B2

Reaction notes

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