Styrene → 4,5-dihydro-N,N-dimethyl-5-phenyl-3-isoxazolecarboxamide

HRID 1528548Notes

Reaction equation

HRID 1528548 reaction equation
[CH3:1][N:2]([CH3:9])[C:3](=[O:8])[C:4](Cl)=[N:5][OH:6].[CH2:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])O.[K+]>C1(C)C=CC=CC=1.O>[CH3:1][N:2]([CH3:9])[C:3]([C:4]1[CH2:10][CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:6][N:5]=1)=[O:8]

Participants

6

Reactant 3

HCID 7501StyreneHCID 516893Potassium BicarbonateHCID 53423335Ethanimidoyl chloride, 2-(dimethylamino)-N-hydroxy-2-oxo-

Product 1

HCID 672359144,5-dihydro-N,N-dimethyl-5-phenyl-3-isoxazolecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a solution of 2-(dimethylamino)-N-hydroxy-2-oxoethanimidoyl chloride (prepared according to the procedure of E. Raleigh, U.S. Pat. No. 3,557,089) (6.0 g, 40 mmol), styrene (6.0 g, 60 mmol) in toluene (15 mL) was added a solution of potassium hydrogen carbonate (5.0 g, 50 mmol) in water (25 mL) over 1 h, while keeping the reaction temperature between 7 and 10° C. The reaction mixture was diluted with 10 mL of toluene, and stirred for an additional 10 minutes. The organic layer was separated and washed with water. The organic layer was concentrated under reduced pressure until no styrene remained to give 8.7 g of the title compound as a light yellow oil. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. customthe reaction temperature between 7 and 10° C
  2. customThe organic layer was separated
  3. washwashed with water
  4. concentrationThe organic layer was concentrated under reduced pressure until no styrene

Sources & evidence

ORD record
ord-9616aafa0e12479ebb6c198923768499
Source dataset
uspto-grants-2015_07
Patent number
US09090604B2

Reaction notes

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