Thionyl Chloride → HCID 20369671, compound

HRID 616317Notes

Reaction equation

HRID 616317 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[N:10]([CH2:13]O)[C:9](=[O:15])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:11](=[O:12])[N:10]([CH2:13][Cl:18])[C:9](=[O:15])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20369664HCID 20369664, compound

Product 1

HCID 20369671HCID 20369671, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent2×

Procedure

2-Phenyl-4-hydroxymethyl-1,2,4-oxadiazolidin-3,5-dione (7.6 grams; 0.0365 mole) dissolved in chloroform (40 ml) and thionyl chloride (8.68 grams; 0.073 mole) dissolved in chloroform (10 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux with stirring for a period of about 2 hours. After this time the reaction mixture was stripped of solvent under reduced pressure, leaving a solid residue. This residue was dissolved in toluene and was distilled to remove unreacted starting material. The remaining product was recrystallized from a hexane-ether mixture to yield the desired product 2-phenyl-4-chloromethyl-1,2,4-oxadiazolidin-3,5-dione.

Workup

  1. additionwere charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. temperaturethermometer and reflux condenser
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux
  6. customleaving a solid residue
  7. distillationwas distilled
  8. customto remove unreacted
  9. customThe remaining product was recrystallized from a hexane-ether mixture

Sources & evidence

ORD record
ord-ba3a1c1038954d37bf6d86ec9cfb26be
Source dataset
uspto-grants-1978_02
Patent number
US04073894

Reaction notes

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