Thionyl Chloride → HCID 20369678, compound

HRID 616320Notes

Reaction equation

HRID 616320 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[N:11]([CH2:14]O)[C:10](=[O:16])[O:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[N:11]([CH2:14][Cl:19])[C:10](=[O:16])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20369675HCID 20369675, compound

Product 1

HCID 20369678HCID 20369678, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6212ChloroformSolvent2×

Procedure

2-(4-Methylphenyl)-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-methylphenyl)-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-e20d26dec3f6412d8491641b13c596ab
Source dataset
uspto-grants-1978_02
Patent number
US04073894

Reaction notes

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