HCID 3303868, compound → HCID 58223543, compound

HRID 386726Notes

Reaction equation

HRID 386726 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([C:21]([F:24])([F:23])[F:22])=[CH2:20])[CH:16]=[C:15]([Cl:25])[CH:14]=1>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[C:17]([C:19]2([C:21]([F:24])([F:22])[F:23])[O:1][N:2]=[C:3]([C:4]3[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=3)[CH2:20]2)[CH:16]=[C:15]([Cl:25])[CH:14]=1

Participants

4

Reactant 2

HCID 3303868HCID 3303868, compoundHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 58223543HCID 58223543, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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. temperatureto reflux for 8 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f8b2202215b94c33924629550f249979
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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