4-Fluoroaniline → Fluoroimide

HRID 596188Notes

Reaction equation

HRID 596188 reaction equation
[Cl:1]/[C:2](=[C:7](\[Cl:12])/[C:8](OC)=[O:9])/[C:3](OC)=[O:4].[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>O>[F:13][C:14]1[CH:20]=[CH:19][C:17]([N:18]2[C:3](=[O:4])[C:2]([Cl:1])=[C:7]([Cl:12])[C:8]2=[O:9])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 3034513Dimethyl 2,3-dichloromaleate

Product 1

HCID 93228FluoroimideYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15g (0.07 mol) of dimethyl 2,3-dichloromaleate was added to 100 ml of water. To the resulting solution 6.7g (0.06 mol) of 4-fluoroaniline was added dropwise over a period of 5 min. at reflux temperatures under agitation. The mixture was then allowed to react for 2 hours at reflux temperatures. Upon cooling the reaction mixture, precipitated crystal was separated by filtration to obtain 15.2g of N-(4-fluorophenyl)-2,3-dichloromaleimide melting at 240°-242° C (not corrected) at a yield of 97.3%. An analysis by gas chromatography showed the product had a purity of 94.1%.

Workup

  1. temperatureat reflux temperatures under agitation
  2. customto react for 2 hours
  3. temperatureat reflux temperatures
  4. temperatureUpon cooling the reaction mixture
  5. customprecipitated crystal
  6. customwas separated by filtration

Sources & evidence

ORD record
ord-f74395ab02ff4db29336f0a0dd4f8f0f
Source dataset
uspto-grants-1977_03
Patent number
US04010182

Reaction notes

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