Styrene → 2-Chloro-1-(4,5-dihydro-5-phenyl-3-isoxazolyl)ethanone

HRID 2095998Notes

Reaction equation

HRID 2095998 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[Cl:14][CH2:15][C:16](=[O:21])[C:17](Cl)=[N:18][OH:19]>C(#N)C>[Cl:14][CH2:15][C:16]([C:17]1[CH2:1][CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:19][N:18]=1)=[O:21]

Participants

5

Reactant 3

HCID 7501StyreneHCID 516892Sodium BicarbonateHCID 68330913-chloro-N-hydroxy-2-oxopropanimidoyl chloride2×

Product 1

HCID 866312462-Chloro-1-(4,5-dihydro-5-phenyl-3-isoxazolyl)ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of styrene (6.79 g, 65.3 mmol) and sodium bicarbonate (32.1 g, powder) in acetonitrile (100 mL), 3-chloro-N-hydroxy-2-oxopropanimidoyl chloride (i.e. the product of Example 7, Step B) (10 g, 64.1 mmol) was added in 10 portions over 20 minutes. The reaction mixture was then stirred for an additional 1 h and filtered. The filtered solid was rinsed with acetonitrile, and the combined filtrates were concentrated under reduced pressure to leave an oil, which was triturated first with hexanes and then with 1-chlorobutane to give 13.6 g of the title compound as a white solid.

Workup

  1. additionwas added in 10 portions over 20 minutes
  2. filtrationfiltered
  3. washThe filtered solid was rinsed with acetonitrile
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. customto leave an oil, which
  6. customwas triturated first with hexanes

Sources & evidence

ORD record
ord-8ed596d88620410d9497cc88db8df72d
Source dataset
uspto-grants-2013_05
Patent number
US08449898B2

Reaction notes

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