Styrene → 4-Phenylazetidin-2-one

HRID 341762Notes

Reaction equation

HRID 341762 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ClS([N:13]=[C:14]=[O:15])(=O)=O.S([O-])([O-])=O.[Na+].[Na+].[OH-].[K+]>C(OCC)C.O>[C:3]1([CH:2]2[NH:13][C:14](=[O:15])[CH2:1]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7501StyreneHCID 14797Potassium HydroxideHCID 24437Sodium SulfiteHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 5688184-Phenylazetidin-2-oneYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

40 g of styrene are slowly dripped into a solution of 54 g of chlorosulphonylisocyanate in 80 cm3 of ethyl ether, maintaining the solvent at reflux temperature. After three hours the reaction mixture is cooled and is added in small quantities to a solution of 48 g of sodium sulphite in 195 cm3 of water, maintaining the temperature at less than 22° C. with an external ice bath and the pH within a range of between 7 and 8 by adding an aqueous solution of potassium hydroxide at 10%. At the end of the addition the mixture is filtered and the organic phase of the filtrate is dried on sodium sulphate and evaporated. 21 g of the desired compound are obtained (yield 38%).

Workup

  1. temperaturemaintaining the solvent
  2. temperatureat reflux temperature
  3. temperatureAfter three hours the reaction mixture is cooled
  4. temperaturemaintaining the temperature at less than 22° C. with an external ice bath
  5. additionAt the end of the addition the mixture
  6. filtrationis filtered
  7. customthe organic phase of the filtrate is dried on sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-ca894595a9f34e9ebf0e692016d12108
Source dataset
uspto-grants-1999_01
Patent number
US05856311

Reaction notes

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