Azobisisobutyronitrile → 2-Oxazolidinone, 3-acetyl-5-chloro-

HRID 1396071Notes

Reaction equation

[C:1]([N:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9])(=[O:3])[CH3:2].S(Cl)([Cl:13])(=O)=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([N:4]1[CH2:8][CH:7]([Cl:13])[O:6][C:5]1=[O:9])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

5.00 g of 3-acetyloxazolidin-2-one were initially charged in 25 ml of carbon tetrachloride and heated to 70° C. under an argon atmosphere. Then, alternately, a solution of 3.46 ml of sulfuryl chloride in 5 ml of carbon tetrachloride and 0.10 g of 2,2′-azobis(2-methylpropionitrile) were added, and then the mixture was stirred at the same temperature for 2 hours. After cooling to room temperature, the clear solution was decanted off from the solid residues, and the solvent was removed under reduced pressure. This gave the product (6.80 g) with a molecular weight of 163.6 g/mol (C5H6ClNO3).

Workup

temperatureAfter cooling to room temperature
customthe clear solution was decanted off from the solid residues
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-a4b3da96da004f8a8730862dbe3bce08
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901114B2

Reaction notes

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