Sodium Hydroxide → HCID 86743839, compound

HRID 1646571Notes

Reaction equation

HRID 1646571 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[N:7]=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=O)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=2)[CH3:9])[O:5][N:4]=1.Cl.[NH2:26][OH:27].[OH-].[Na+]>C(O)C.O>[CH3:1][N:2]([CH3:24])[C:3]1[N:7]=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[N:26][OH:27])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=2)[CH3:9])[O:5][N:4]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 15676082HCID 15676082, compound

Product 1

HCID 86743839HCID 86743839, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To 3-dimethylamino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole (1.0 g, 3.11 mmol) in ethanol (10 ml) were added hydroxylamine hydrochloride (0.25 g, 3.45 mmol) in water (2 ml) and sodium hydroxide (0.40 g, 9.5 mmol) in water (2 ml). After reflux with stirring for 24 h, the mixture was poured upon ice water and extracted with ethyl acetate. The ethyl acetate extracts were washed with saturated NaCl aq. dried with anhydrous magnesium salfate, and evaporated under redused pressure to a residue, which was chromatographed to afford 3-dimethylamino-5-(1-(3-(α-hydroxyiminobenzyl)phenyl)ethyl)-1,2,4-oxadiazole (0.873 g, 84% yield) as oily substance: NMR(CDCl3)δ1.66(d)+1.77(d) (3H), 2.98(s, 6H), 4.20(m, 1H), 7.22-7.55(m, 9H) ppm; IR(neat) 3700-3100, 1600, 1405 cm-1.

Workup

  1. temperatureAfter reflux
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate extracts were washed with saturated NaCl aq.
  4. dry with materialdried with anhydrous magnesium salfate
  5. customevaporated under redused pressure to a residue, which
  6. customwas chromatographed

Sources & evidence

ORD record
ord-8db67bf7f1a348fc81d279f1e1ce86f9
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

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