Hydroxyamine hydrochloride → (NE)-N-[[4-bromo-2-[3-[5-phenyl-4-(trifluoromethyl)-1,2-oxazol-3-yl]prop-2-ynoxy]phenyl]methylidene]hydroxylamine

HRID 1506438Notes

Reaction equation

HRID 1506438 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH2:11][C:12]#[C:13][C:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:16][N:15]=2)[CH:3]=1.Cl.[NH2:30][OH:31].C([O-])(=O)C.[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:30]/[OH:31])=[C:4]([O:10][CH2:11][C:12]#[C:13][C:14]2[C:18]([C:19]([F:21])([F:20])[F:22])=[C:17]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:16][N:15]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866699074-Bromo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)prop-2-ynyloxy)benzaldehyde

Product 1

HCID 87294070(NE)-N-[[4-bromo-2-[3-[5-phenyl-4-(trifluoromethyl)-1,2-oxazol-3-yl]prop-2-ynoxy]phenyl]methylidene]hydroxylamineYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-bromo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)prop-2-ynyloxy)benzaldehyde (Preparation 62D, 0.050 g, 0.111 mmol), hydroxylamine hydrochloride (9.26 mg, 0.133 mmol), and sodium acetate (0.018 g, 0.222 mmol) in methanol (2.0 mL) was heated at reflux for 30 min. The solvent was removed under reduce pressure, and the residue was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded (E)-4-bromo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)prop-2-ynyloxy)benzaldehyde oxime (0.050 g, 0.107 mmol, 97% yield) as a white solid. The product had an HPLC with a ret. time=3.26 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=466.8.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 min
  3. customThe solvent was removed
  4. additionthe residue was diluted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-94b3a796633f4bb38f1b5aa9560f9d56
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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