HCID 19475, compound → HCID 3303868, compound

HRID 386725Notes

Reaction equation

HRID 386725 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][CH:3]=1.[Cl:11]N1C(=O)CCC1=O>CN(C)C=O.C(OC)(C)(C)C>[OH:8][N:7]=[C:6]([Cl:11])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 19475HCID 19475, compoundHCID 31398Chlorosuccinimide

Product 1

HCID 3303868HCID 3303868, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 4-methylbenzaldehyde oxime (2 g) and N-chlorosuccinimide (2.17 g) in dimethylformamide (20 mL) was stirred for one hour at 55° C. After the reaction solution was diluted with t-butylmethylether, the solution was washed with water and saturated brine. The organic layer was dried over-anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain N-hydroxy-4-methylbenzene carboximidoyl chloride (2 g). A solution of resultant N-hydroxy-4-methylbenzene carboximidoyl chloride and 1,3-dichloro-5-[1-(trifluoromethyl)-vinyl]benzene (5.3 g) in toluene (50 mL) was heated to reflux for 8 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to obtain [5-(3,5-dichlorophenyl) 3-(4-methylphenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (5.0 g).

Workup

  1. washthe solution was washed with water and saturated brine
  2. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-69a86a39bd164f45a18fd23d24ef55cd
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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