Triethylamine → HCID 21536149, compound

HRID 1077282Notes

Reaction equation

HRID 1077282 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[NH:11][C:10](=[O:14])[O:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:24]=1[C:25](Cl)=[O:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12](=[O:13])[N:11]([C:25](=[O:26])[C:24]3[C:23]([Cl:22])=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:32])[C:10](=[O:14])[O:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 21536154HCID 21536154, compound

Product 1

HCID 21536149HCID 21536149, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-(4-Chlorophenyl)-1,2,4-oxadiazolidin-3,5-dione (3.8 grams; 0.018 mole), toluene (50 ml) and triethylamine (2.8 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2,6-Dichlorobenzoyl chloride (4.19 grams) dissolved in toluene (10 ml) is then added to the reaction flask and the resulting mixture is heated at reflux with stirring for a period of about 3 days. 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, is filtered and is stripped of solvent under reduced pressure. The residue is washed with a hexane-ether mixture to yield a brown solid. This solid is recrystallized from a benzene-hexane mixture to yield the desired product 2-(4-chlorophenyl)-4-(2,6-dichlorobenzoyl)-1,2,4-oxadiazolidin-3,5-dione having a melting point of 112° to 116°C.

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. filtrationis filtered
  10. washThe residue is washed with a hexane-ether mixture
  11. customto yield a brown solid
  12. customThis solid is recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-6ec4603eb76945f1b8f3fa12c4619b2d
Source dataset
uspto-grants-1976_05
Patent number
US03959478

Reaction notes

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