Urea → 5-Fluoroisoindoline-1,3-dione

HRID 2118828Notes

Reaction equation

HRID 2118828 reaction equation
N[C:2]([NH2:4])=[O:3].[F:5][C:6]1[CH:7]=[C:8]2C(=O)O[C:10](=[O:11])[C:9]2=[CH:15][CH:16]=1>>[F:5][C:6]1[CH:16]=[C:15]2[C:2](=[O:3])[NH:4][C:10](=[O:11])[C:9]2=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 1176UreaHCID 675721,3-Isobenzofurandione, 5-fluoro-

Product 1

HCID 108990385-Fluoroisoindoline-1,3-dione

Conditions

Temperature
160 °C

Procedure

8.2 parts (0.137 mole) of urea are added to 185 parts of the distillate (containing 43.4 parts (0.261 mole) of 4-fluorophthalic anhydride). The mixture is stirred for 3 hours at 135°-140° C., after which the evolution of gas is complete, and is finally heated for a further 10 minutes at 160° C. The solvent is distilled off (144.2 parts) at 115°-130° C. and under 0.3 mbar. According to gas chromatography, it contains 9.6 parts of 4-fluorophthalimide. The distillation residue is stirred with water, and the product is filtered off under suction, washed and dried, 31 parts of 4-fluorophthalimide of melting point 174°-176° C. being obtained. The total yield is 40.6 parts (94.2% of theory) of 4-fluorophthalimide.

Workup

  1. distillationThe solvent is distilled off (144.2 parts) at 115°-130° C.
  2. stirringThe distillation residue is stirred with water
  3. filtrationthe product is filtered off under suction
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-f58cfbef19f6411fa6369cda41cfe578
Source dataset
uspto-grants-1987_07
Patent number
US04680412

Reaction notes

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