4-Fluoroaniline → Fluoroimide

HRID 596179

Reaction equation

HRID 596179 reaction equation
[Cl:1]/[C:2](=[C:6](\[Cl:10])/[C:7](O)=[O:8])/[C:3](O)=[O:4].[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>O>[F:11][C:12]1[CH:18]=[CH:17][C:15]([N:16]2[C:3](=[O:4])[C:2]([Cl:1])=[C:6]([Cl:10])[C:7]2=[O:8])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 97314-Fluoroaniline2×HCID 6437972,3-Dichloromaleic acid

Product 1

HCID 93228FluoroimideYield 97.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 g (0.06 mol) of 2,3-dichloromaleic acid was dissolved in 100 ml of water. Then, to the resulting solution 5.55g (0.05 mol) of 4-fluoroaniline was added dropwise over a period of 5 min. at reflux temperatures under agitation. Upon addition of 4 -fluoroaniline, a white crystal separated out immediately but the reaction was allowed to preceed for two hours. After cooling, the crystal was separated by filtration and fully rinsed with water to obtain 12.7g (yield, 97.7%) of N-(4-fluorophenyl)-2,3-dichloromaleimide (Sample No. 1) having an average grain size of 10μ. An analysis by gas chromatography showed that the N-(4-fluorophenyl)-2,3-dichloromaleimide had a purity of 96.2%.

Workup

  1. temperatureat reflux temperatures under agitation
  2. customa white crystal separated out immediately
  3. temperatureAfter cooling
  4. customthe crystal was separated by filtration
  5. washfully rinsed with water

Sources & evidence

ORD record
ord-848a2ba1c81d40caa92dd79dae27eb59
Source dataset
uspto-grants-1977_03
Patent number
US04010182

Linked notes

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