Triethylamine → HCID 21536163, compound

HRID 1077293Notes

Reaction equation

HRID 1077293 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[NH:11][C:10](=[O:14])[O:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[F:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:24]=1[C:25](Cl)=[O:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[N:11]([C:25](=[O:26])[C:24]3[C:23]([F:22])=[CH:31][CH:30]=[CH:29][C:28]=3[F:32])[C:10](=[O:14])[O:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 21536150HCID 21536150, compound

Product 1

HCID 21536163HCID 21536163, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-(3-Chlorophenyl)-1,2,4-oxadiazolidin-3,5-dione (0.03 mole), toluene (100 ml) and triethylamine (5 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2,6-Difluorobenzoyl chloride (0.03 mole) dissolved in toluene (20 ml) is then added to the reaction flask and the resulting mixture is heated at reflux with stirring for a period of about 24 hours. After this time the reaction mixture is filtered and the filtrate is washed with water, dilute hydrochloric acid and with aqueous sodium bicarbonate. The washed solution is then dried over anhydrous magnesium sulfate. The dried solution is stripped of solvent under reduced pressure leaving a solid residue. The residue is recrystallized to yield the desired product 2-(3-chlorophenyl)-4-(2,6-difluorobenzoyl)-1,2,4-oxadiazolidin-3,5-dione.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionis then added to the reaction flask
  4. temperaturethe resulting mixture is heated
  5. temperatureat reflux
  6. filtrationAfter this time the reaction mixture is filtered
  7. washthe filtrate is washed with water, dilute hydrochloric acid and with aqueous sodium bicarbonate
  8. dry with materialThe washed solution is then dried over anhydrous magnesium sulfate
  9. customleaving a solid residue
  10. customThe residue is recrystallized

Sources & evidence

ORD record
ord-44b887af641c4938bfc2c2108e302a72
Source dataset
uspto-grants-1976_05
Patent number
US03959478

Reaction notes

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