4-Fluoroaniline → Fluoroimide

HRID 596180

Reaction equation

HRID 596180 reaction equation
[Cl:1][C:2]1[C:3]([O:5][C:6](=O)[C:7]=1[Cl:8])=[O:4].[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>O>[F:10][C:11]1[CH:17]=[CH:16][C:14]([N:15]2[C:3](=[O:4])[C:2]([Cl:1])=[C:7]([Cl:8])[C:6]2=[O:5])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 70728Dichloromaleic anhydride

Product 1

HCID 93228FluoroimideYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10g (0.06 mol) of 2,3-dichloromaleic anhydride was dissolved in 100 ml of water. Then, to the resulting solution 5.55g (0.05mol) of 4-fluoroaniline was added dropwise over a period of 5 min. at room temperatures under agitation. The mixture was allowed to react for 2 hours at 80° C. Upon cooling the reaction mixture, a crystal was separated out, which was then separated by filtration to obtain 12.8g of N-(4-fluorophenyl)-2,3-dichloromaleimide melting at 239°-242° C (not corrected) at a yield of 98.4%. An analysis by gas chromatography showed the product had a purity of 98.7%.

Workup

  1. customto react for 2 hours at 80° C
  2. temperatureUpon cooling the reaction mixture
  3. customa crystal was separated out
  4. customwhich was then separated by filtration

Sources & evidence

ORD record
ord-2bf9eb95a6c947c5967ad7cb37236780
Source dataset
uspto-grants-1977_03
Patent number
US04010182

Linked notes

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