Triethylamine → HCID 178423542, compound

HRID 216004Notes

Reaction equation

HRID 216004 reaction equation
Cl.[NH2:2][OH:3].[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2([C:26]([F:29])([F:28])[F:27])[O:16][N:15]=[C:14]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([CH3:25])[CH:18]=3)[CH2:13]2)[CH:8]=[C:9]([Cl:11])[CH:10]=1.C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2([C:26]([F:27])([F:29])[F:28])[O:16][N:15]=[C:14]([C:17]3[CH:24]=[CH:23][C:20]([C:21]([NH:2][OH:3])=[NH:22])=[C:19]([CH3:25])[CH:18]=3)[CH2:13]2)[CH:8]=[C:9]([Cl:11])[CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochloride2×HCID 582001084-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-methylbenzonitrile

Product 1

HCID 178423542HCID 178423542, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

Hydroxylamine hydrochloride (0.27 g) was added to a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzonitrile (1.1 g) (Example I4) and triethylamine (0.65 ml) in ethanol (30 ml). The reaction mixture was heated to 85° C. for 20 hours. The reaction mixture was allowed to cool to ambient temperature before adding more hydroxylamine hydrochloride (0.078 g). The reaction mixture was again heated to 85° C. for 3 hours. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1) to give Compound No. A1 of Table A (0.84 g) as a white solid.

Workup

  1. temperatureto cool to ambient temperature
  2. temperatureThe reaction mixture was again heated to 85° C. for 3 hours
  3. temperatureto cool to ambient temperature
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)
  8. customto give Compound No

Sources & evidence

ORD record
ord-e47d3076d5e747958bac0ec92f5418a5
Source dataset
uspto-grants-2012_06
Patent number
US08193221B2

Reaction notes

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