Triethylamine → 1-(2,6-Dichloro-4-trifluoromethylphenyl)-5-hydroxyaminomethylideneamino-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazole

HRID 429264Notes

Reaction equation

HRID 429264 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([N:18]=[CH:19]OC)=[C:16]([S:22]([C:24]([F:27])([F:26])[F:25])=[O:23])[C:15]([C:28]2[N:32]=[CH:31][O:30][N:29]=2)=[N:14]1.Cl.[NH2:34][OH:35].O1CCOCC1.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([N:18]=[CH:19][NH:34][OH:35])=[C:16]([S:22]([C:24]([F:25])([F:26])[F:27])=[O:23])[C:15]([C:28]2[N:32]=[CH:31][O:30][N:29]=2)=[N:14]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 312751,4-Dioxane2×HCID 443297Hydroxyamine hydrochlorideHCID 570711311-(2,6-Dichloro-4-trifluoromethylphenyl)-5-methoxymethylideneamino-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazole

Product 1

HCID 1360701921-(2,6-Dichloro-4-trifluoromethylphenyl)-5-hydroxyaminomethylideneamino-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazoleYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methoxymethylideneamino-3-(1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazole (720 mg, 1.38 mmol) were added hydroxylamine hydrochloride (240 mg, 3.45 mmol), dioxane (2.0 ml) and triethylamine (0.40 ml, 2.90 mmol), and then the mixture was stirred at room temperature. Five hours after stirring, triethylamine (0.4 ml, 2.90 mmol) and dioxane (1.0 ml) were further added, followed by stirring at room temperature for 66 hours. After 40 ml of ethyl acetate was added, the organic layer was washed three times with 30 ml of an aqueous saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain a pale yellow oil. The oil was purified by subjecting to silica gel preparative TLC [developing solvent: mixed solvent of chloroform and ethyl acetate (volume ratio=10:1)] to obtain 284 mg (0.54 mmol) of the title compound as a colorless crystal. Yield 55%.

Workup

  1. stirringFive hours after stirring
  2. stirringby stirring at room temperature for 66 hours
  3. washthe organic layer was washed three times with 30 ml of an aqueous saturated sodium chloride solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customto obtain a pale yellow oil
  7. customThe oil was purified
  8. additionby subjecting to silica gel preparative TLC [developing solvent: mixed solvent of chloroform and ethyl acetate (volume ratio=10:1)]

Sources & evidence

ORD record
ord-494fd4722540459790705fe33194ae7c
Source dataset
uspto-grants-2001_11
Patent number
US06316477B1

Reaction notes

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