4-Fluoroaniline → Fluoroimide

HRID 596183

Reaction equation

HRID 596183 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][C:10]1[C:11]([O:13][C:14](=O)[C:15]=1[Cl:16])=[O:12]>O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:11](=[O:12])[C:10]([Cl:9])=[C:15]([Cl:16])[C:14]2=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 70728Dichloromaleic anhydride

Product 1

HCID 93228FluoroimideYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

5.55g (0.05 mol) of 4-fluoroaniline was emulsified in 150 ml of water. Then to the resulting emulsion 10g (0.06 mol) of 2,3-dichloromaleic anhydride in 50 ml of water was added dropwise over a period of 30 min. at room temperatures under agitation. The mixture was then allowed to react at reflux temperatures. Upon cooling the reaction mixture, a crystal was removed out, which was separated by filtration to obtain 12.9g of N-(4-fluorophenyl)-2,3-dichloromaleimide melting at 240°-243° C (not corrected) at a yield of 99.1%. An analysis by gas chromatography showed the product had a purity of 98.6%.

Workup

  1. customto react
  2. temperatureat reflux temperatures
  3. temperatureUpon cooling the reaction mixture
  4. customa crystal was removed out
  5. customwhich was separated by filtration

Sources & evidence

ORD record
ord-843fb8ced79a43738e787705d73b5cc0
Source dataset
uspto-grants-1977_03
Patent number
US04010182

Linked notes

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