4-Fluoroaniline → Fluoroimide

HRID 596181

Reaction equation

HRID 596181 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 91.5%

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 (0.05 mol) of 4-fluoroaniline was added dropwise over a period of 5 min. at room temperatures under agitation. The mixture was then allowed to react for 15 hours at 60° C. Upon cooling the reaction mixture, precipitated crystal was separated by filtration to obtain 11.9g of N-(4-fluorophenyl)-2,3-dichloromaleimide melting at 239°-242° C (not corrected) at a yield of 91.5%. An analysis by gas chromatography showed the product had a purity of 97.9%.

Workup

  1. customto react for 15 hours at 60° C
  2. temperatureUpon cooling the reaction mixture
  3. customprecipitated crystal
  4. customwas separated by filtration

Sources & evidence

ORD record
ord-e77796bf101342a2a80e47e56a04447c
Source dataset
uspto-grants-1977_03
Patent number
US04010182

Linked notes

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