Triethylamine → 5-(3,5-Dichloro-phenyl)-3-(4-fluoro-naphthalen-1-yl)-5-trifluoromethyl-4,5-dihydro-isoxazole

HRID 388376Notes

Reaction equation

HRID 388376 reaction equation
ClN1C(=O)CCC1=O.[F:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]=[N:21][OH:22])=[CH:12][CH:11]=1.[Cl:23][C:24]1[CH:29]=[C:28]([C:30]([C:32]([F:35])([F:34])[F:33])=[CH2:31])[CH:27]=[C:26]([Cl:36])[CH:25]=1.C(N(CC)CC)C>CN(C=O)C.O>[Cl:23][C:24]1[CH:29]=[C:28]([C:30]2([C:32]([F:35])([F:33])[F:34])[O:22][N:21]=[C:20]([C:13]3[C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:10]([F:9])=[CH:11][CH:12]=3)[CH2:31]2)[CH:27]=[C:26]([Cl:36])[CH:25]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 866581594-Fluoro-naphthalene-1-carbaldehyde oxime

Product 1

HCID 866581605-(3,5-Dichloro-phenyl)-3-(4-fluoro-naphthalen-1-yl)-5-trifluoromethyl-4,5-dihydro-isoxazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

N-chlorosuccinimid (4.7 g) is added to a solution of 4-fluoro-naphthalene-1-carbaldehyde oxime (6.6 g, example 5 step A) in DMF (50 ml). After 45 minutes at 40° C., the reaction is cooled down to 0° C. and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene, (8.4 g, example 1 step A) and triethylamine (5.4 ml) are added. The reaction is then further reacted at room temperature for 3 hours. Water is added (50 ml) and the reaction mixture is extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is dissolved in dichloromethane and filtered over a pad of silica gel to yield 5-(3,5-dichloro-phenyl)-3-(4-fluoro-naphthalen-1-yl)-5-trifluoromethyl-4,5-dihydro-isoxazole as a beige solid.

Workup

  1. customThe reaction is then further reacted at room temperature for 3 hours
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. washThe organic phase is washed with a saturated aqueous solution of NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude product is dissolved in dichloromethane
  7. filtrationfiltered over a pad of silica gel

Sources & evidence

ORD record
ord-f6ef0ab253894c17915d06848d68b93e
Source dataset
uspto-grants-2013_02
Patent number
US08377942B2

Reaction notes

Loading…