Hydroxyamine hydrochloride → HCID 86666623, compound

HRID 587840Notes

Reaction equation

HRID 587840 reaction equation
[C:1]([C:4]1[CH:31]=[CH:30][C:7]([C:8]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([C:18]([F:27])([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])=[CH:13][C:12]=2[CH2:28][CH3:29])=[O:9])=[CH:6][CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[Na+].Cl.[NH2:38][OH:39]>C(O)C.O>[CH2:28]([C:12]1[CH:13]=[C:14]([C:18]([F:27])([C:19]([F:22])([F:20])[F:21])[C:23]([F:25])([F:24])[F:26])[CH:15]=[C:16]([CH3:17])[C:11]=1[NH:10][C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([C:1](=[N:38][OH:39])[CH3:2])=[CH:31][CH:30]=1)[CH3:29]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86666624HCID 86666624, compound

Product 1

HCID 86666623HCID 86666623, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Acetyl-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-benzamide (2.2 g) was dissolved in ethanol (15 ml) and water (15 ml). To the solution, sodium acetate (0.6 g) and hydroxylamine hydrochloride (0.30 g) were added and the mixture was refluxed under heating for 4 hours. The reaction solution was extracted twice with ethyl acetate. The organic phases were combined, washed with water and dried over anhydrous magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-4-[N-hydroxyethaneimidoyl]benzamide (2.1 g, yield 96%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. extractionThe reaction solution was extracted twice with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering off the drying agent
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4a4f83598a7f4666a815939c5ead6845
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

Loading…