Triethylamine → 3-(5-(3,5-Dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-3-isoxazolyl)nitrobenzene

HRID 1958652Notes

Reaction equation

HRID 1958652 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH:7]=[N:8][OH:9])([O-:3])=[O:2].ClN1C(=O)CCC1=O.[Cl:21][C:22]1[CH:27]=[C:26]([C:28]([C:30]([F:33])([F:32])[F:31])=[CH2:29])[CH:25]=[C:24]([Cl:34])[CH:23]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[Cl:21][C:22]1[CH:27]=[C:26]([C:28]2([C:30]([F:33])([F:31])[F:32])[O:9][N:8]=[C:7]([C:6]3[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[CH2:29]2)[CH:25]=[C:24]([Cl:34])[CH:23]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 2191323-NitrobenzaldoximeHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 593556103-(5-(3,5-Dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-3-isoxazolyl)nitrobenzeneYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

3-Nitro-benzaldehyde oxime (commercially available) (6.15 g, 37.0 mmol) and N-chlorosuccinimide (“NCS”) (4.94 g, 37.0 mmol) were dissolved in N,N-dimethylformamide (65 ml). This mixture was stirred at ambient temperature for 90 minutes. A solution of 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (which was made as described, for example, in WO 05/085216) (8.53 mg, 37.0 mmol) and triethylamine (5.15 ml, 37.0 mmol) in N,N-dimethylformamide (70 ml) was added and the reaction mixture was stirred at ambient temperature for 18 hours. Water (300 ml) and ethyl acetate (300 ml) were added. The phases were separated and the organic phase was washed twice with water. The aqueous phases were extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1) to give 5-(3,5-dichloro-phenyl)-3-(3-nitro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (14.5 g, 97% yield). The residue was used without further purification or analysis.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 18 hours
  2. customThe phases were separated
  3. washthe organic phase was washed twice with water
  4. extractionThe aqueous phases were extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-e6a8f3bbb03a48b78f3f2d0e3f8d4962
Source dataset
uspto-grants-2013_04
Patent number
US08410145B2

Reaction notes

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