Hydroxyamine hydrochloride → HCID 178526353, compound

HRID 898007Notes

Reaction equation

HRID 898007 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[F:21])=S)=[CH:4][CH:3]=1.Cl.[NH2:23][OH:24].C(=O)(O)[O-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[N:23][OH:24])[C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[F:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 22346721HCID 22346721, compound

Product 1

HCID 178526353HCID 178526353, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N1-(4-bromophenyl)-2-fluoro-4-(trifluoromethyl)-1-benzenecarbothioamide (2.50 g, 0.00663 mol), hydroxylamine hydrochloride (0.65 g, 0.00928 mol) and sodium bicarbonate (0.78 g, 0.00928 mol) was heated in absolute ethanol (25 mL) at reflux under nitrogen atmosphere for 14 hours. The reaction mixture was cooled to ambient temperature, the solvent was removed under reduced pressure and the residue partitioned between saturated solution of sodium bicarbonate in water (50 mL) and ethyl acetate (50 mL). The organic phase was washed with brine, dried with magnesium sulfate and concentrated. The residue was suspended in cold n-heptane and the precipitate was collected by filtration and dried to yield N1-(4-bromophenyl)-2-fluoro-4-(trifluoromethyl)-1-benzeneamidoxime (2.35 g, 0.00625 mol) as an off-white solid.

Workup

  1. temperatureat reflux under nitrogen atmosphere for 14 hours
  2. customthe solvent was removed under reduced pressure
  3. customthe residue partitioned between saturated solution of sodium bicarbonate in water (50 mL) and ethyl acetate (50 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. filtrationthe precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-10fe959aad7945dd825d7813bf5998b8
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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