Water → HCID 136109406, compound

HRID 429253

Reaction equation

HRID 429253 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:23]([F:26])([F:25])[F:24])=[O:22].Cl.[NH2:28][OH:29].C(N(CC)CC)C.O>O1CCOCC1.C(OCC)(=O)C.CCCCCC>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19](=[N:28][OH:29])[NH2:20])[C:3]=1[S:21]([C:23]([F:25])([F:24])[F:26])=[O:22]

Participants

8

Reactant 4

HCID 962WaterHCID 3352FipronilHCID 8471Triethylamine2×HCID 443297Hydroxyamine hydrochloride2×

Product 1

HCID 136109406HCID 136109406, compoundYield 65.5%

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole (500 mg, 1.1 mmol) and hydroxylamine hydrochloride (79 mg, 1.1 mmol) were dissolved in 5 ml of dioxane, and then triethylamine (115 mg, 1.1 mmol) was added at room temperature. After the mixture was stirred at room temperature for 6 hours, hydroxylamine hydrochloride (79 mg, 1.1 mmol) and triethylamine (115 mg, 1.1 mmol) were further added, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into 100 ml of iced water and extracted with 100 ml of ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated to obtain a brown oily substance. This oily substance was subjected to silica gel column chromatography [eluent: mixed solvent of n-hexane and ethyl acetate (volume ratio=3:1)] to obtain 340 mg (0.72 mmol) of the title compound as a colorless crystal. Yield 63%.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionextracted with 100 ml of ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain a brown oily substance

Sources & evidence

ORD record
ord-7478df3361dc4c8b894a280c733d45fc
Source dataset
uspto-grants-2001_11
Patent number
US06316477B1

Linked notes

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