Thionyl Chloride → HCID 20369652, compound

HRID 616322Notes

Reaction equation

HRID 616322 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[N:12]([CH2:15]O)[C:11](=[O:17])[O:10]2)=[CH:5][CH:4]=1.S(Cl)([Cl:20])=O>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[N:12]([CH2:15][Cl:20])[C:11](=[O:17])[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20369679HCID 20369679, compound

Product 1

HCID 20369652HCID 20369652, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6212ChloroformSolvent2×

Procedure

2-(4-Methoxyphenyl)-4-hydroxymethyl-1,2,4-oxadiazolidin-3,5-dione (0.03 mole) dissolved in chloroform (40 ml) and thionyl chloride (0.06 mole) dissolved in chloroform (10 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux for a period of about 2 hours. After this time the reaction mixture is stripped of solvent under reduced pressure, leaving a residue. This residue is dissolved in toluene, and the toluene solution is stripped of solvent and unreacted starting materials to yield the desired product 2-(4-methoxyphenyl)-4-chloromethyl-1,2,4-oxadiazolidin-3,5-dione as the residue.

Workup

  1. additionare charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. temperaturethermometer and reflux condenser
  4. temperatureThe reaction mixture is heated
  5. temperatureat reflux for a period of about 2 hours
  6. customleaving a residue

Sources & evidence

ORD record
ord-e7fbf7c181e749bca3a8410d9e276c0b
Source dataset
uspto-grants-1978_02
Patent number
US04073894

Reaction notes

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