Thionyl Chloride → HCID 20369670, compound

HRID 616328Notes

Reaction equation

HRID 616328 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[N:13]1[C:17](=[O:18])[N:16]([CH2:19]O)[C:15](=[O:21])[O:14]1)([O-:3])=[O:2].S(Cl)([Cl:24])=O>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[N:13]1[C:17](=[O:18])[N:16]([CH2:19][Cl:24])[C:15](=[O:21])[O:14]1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 20369666HCID 20369666, compound

Product 1

HCID 20369670HCID 20369670, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6212ChloroformSolvent2×

Procedure

2-(2,6-Dinitrophenyl)-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. Aftr 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-(2,6-dinitrophenyl)-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-d02be5d14c8c4b1eb759ae6cc92b1d32
Source dataset
uspto-grants-1978_02
Patent number
US04073894

Reaction notes

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