Hydroxyamine hydrochloride → HCID 178526352, compound

HRID 897878Notes

Reaction equation

HRID 897878 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=S)=[CH:4][CH:3]=1.Cl.[NH2:19][OH:20].C(=O)(O)[O-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[N:19][OH:20])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 22346994HCID 22346994, compound

Product 1

HCID 178526352HCID 178526352, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N1-(4-bromophenyl)-2-fluoro-1-benzenecarbothioamide (1.56 g, 0.00505 mol), hydroxylamine hydrochloride (0.44 g, 0.00631 mol) and sodium bicarbonate (0.53 g, 0.00631 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 diethyl ether and the precipitate was collected by filtration and dried to yield N1-(4-bromophenyl)-2-fluoro-1-benzeneamidoxime (1.21 g, 0.00392 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-27399fc8dbf7472f9f4674876b3577dc
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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