Maleic Anhydride → HCID 14181821, compound

HRID 1110852Notes

Reaction equation

HRID 1110852 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.C([Br:19])(=O)C>C1(C)C=CC=CC=1>[Br:19][CH:2]1[CH2:3][C:4](=[O:5])[N:13]([C:12]2[CH:14]=[CH:15][C:9]([F:8])=[CH:10][CH:11]=2)[C:1]1=[O:7]

Participants

5

Reactant 3

HCID 7923Maleic AnhydrideHCID 97314-FluoroanilineHCID 10482Acetyl bromide

Product 1

HCID 14181821HCID 14181821, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
30 °C

Procedure

29.4 g. (0.3 mole) maleic acid anhydride were dissolved in 300 ml. toluene and a solution of 33.3 g. (0.3 mole) 4-fluoroaniline in 100 ml. toluene added thereto at 30° C. The hemi-anilide rapidly precipitated out. For the completion of the reaction, the mixture was heated for 2 hours to 100° C., then cooled, the precipitated product filtered off, washed and dried. The yield of hemi-anilide was quantitative. The hemianilide was suspended in acetic acid ethyl ester and 43 g. (0.35 mole) acetyl bromide added thereto. The reaction was carried out by stirring at 30° C. (2 hrs.) and by subsequent 2 hours heating to reflux, thereafter the solvent was distilled off and the residue crystallised. The yield amounted to 69.2 g. (corresponding to 85.5% of theory). The product displayed a melting point of 154° C.

Workup

  1. customat 30° C
  2. customThe hemi-anilide rapidly precipitated out
  3. customFor the completion of the reaction
  4. temperaturethe mixture was heated for 2 hours to 100° C.
  5. temperaturecooled
  6. filtrationthe precipitated product filtered off
  7. washwashed
  8. customdried
  9. temperatureby subsequent 2 hours heating
  10. temperatureto reflux
  11. distillationthe solvent was distilled off
  12. customthe residue crystallised

Sources & evidence

ORD record
ord-59297a8ec08b474ea4c9265f0ce420a6
Source dataset
uspto-grants-1990_12
Patent number
US04977183

Reaction notes

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