Triethylamine → 1-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-1H-[1,2,4]triazole

HRID 388366Notes

Reaction equation

HRID 388366 reaction equation
ClN1C(=O)CCC1=O.[N:9]1([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]=[N:25][OH:26])=[CH:16][CH:15]=2)[CH:13]=[N:12][CH:11]=[N:10]1.[Cl:27][C:28]1[CH:33]=[C:32]([C:34]([C:36]([F:39])([F:38])[F:37])=[CH2:35])[CH:31]=[C:30]([Cl:40])[CH:29]=1.C(N(CC)CC)C>CN(C=O)C.O>[Cl:27][C:28]1[CH:33]=[C:32]([C:34]2([C:36]([F:39])([F:37])[F:38])[O:26][N:25]=[C:24]([C:17]3[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:14]([N:9]4[CH:13]=[N:12][CH:11]=[N:10]4)=[CH:15][CH:16]=3)[CH2:35]2)[CH:31]=[C:30]([Cl:40])[CH:29]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 866581564-[1,2,4]Triazol-1-yl-naphthalene-1-carbaldehyde oxime

Product 1

HCID 468423961-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-1H-[1,2,4]triazoleYield 64.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-chlorosuccinimid (220 mg) is added to a solution of 4-[1,2,4]triazol-1-yl-naphthalene-1-carbaldehyde oxime (390 mg) in DMF (5 ml). After 45 minutes at 40° C., the reaction is cold down to 0° C., and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (394 mg, Example 1, step A) and triethylamine (0.25 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 two times with ethyl acetate. The organic phase is extracted, with a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC: to yield 1-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-1H-[1,2,4]triazole (500 mg) as beige crystals. MS (HPLC/MS): 477 (MH+). Retention time: 5.20 min.

Workup

  1. customis cold down to 0° C.
  2. customThe reaction is then further reacted at room temperature for 3 hours
  3. extractionthe reaction mixture is extracted two times with ethyl acetate
  4. extractionThe organic phase is extracted, with a saturated aqueous solution of NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-82f193da01f54203bf99b8c337c34dc2
Source dataset
uspto-grants-2013_02
Patent number
US08377942B2

Reaction notes

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