Water → HCID 136067614, compound

HRID 429254Notes

Reaction equation

HRID 429254 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][CH3:22].Cl.[NH2:24][OH:25].C(N(CC)CC)C.O>O1CCOCC1.C(Cl)(Cl)Cl.CCCCCC>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:17])([F:15])[F:16])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19](=[N:24][OH:25])[NH2:20])[C:3]=1[S:21][CH3:22]

Participants

8

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 443297Hydroxyamine hydrochloride2×HCID 18005433HCID 18005433, compound

Product 1

HCID 136067614HCID 136067614, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthiopyrazole (7.5 g, 20.4 mmol) and hydroxylamine hydrochloride (1.83 g, 25.5 mmol) were dissolved in 75 ml of dioxane, and then triethylamine (2.5 g, 24.5 mmol) was added at room temperature. After the mixture was stirred at room temperature for 29 hours, hydroxylamine hydrochloride (720 mg, 10.1 mmol) and triethylamine (1.0 g, 10.2 mmol) were further added, followed by stirring at room temperature for 22 hours. The reaction mixture was poured into 200 ml of iced water and extracted with 250 ml of ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated to obtain a yellow crystal. The crystal was subjected to silica gel column chromatography [eluent: mixed solvent of n-hexane and chloroform (volume ratio=1:1)] to obtain 6.98 g (17.4 mmol) of the title compound as a colorless crystal. Yield 85%.

Workup

  1. stirringby stirring at room temperature for 22 hours
  2. extractionextracted with 250 ml of ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain a yellow crystal

Sources & evidence

ORD record
ord-eb38a8c43eb7415bb5dde3fae85c3e26
Source dataset
uspto-grants-2001_11
Patent number
US06316477B1

Reaction notes

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