O-Methylhydroxylamine hydrochloride → HCID 54092853, compound

HRID 1646570Notes

Reaction equation

HRID 1646570 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=O)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)[CH3:8])[O:4][N:3]=1.Cl.[CH3:24][O:25][NH2:26]>N1C=CC=CC=1>[NH2:1][C:2]1[N:6]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[N:26][O:25][CH3:24])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)[CH3:8])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 156760943-Amino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole

Product 1

HCID 54092853HCID 54092853, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 3-amino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole (0.60 g, 2.0 mmol) in pyridine (10 ml) was added methoxyamine hydrochloride (0.224 g, 2.7 mol). After reflux with stirring for 18 h, the mixture was poured upon ice water, extracted with ethylacetate. The extracts were washed with water, dried and anhydrous sodium sulfate, and evaporated under reduced pressure to a residue, which was chromatographed to afford 3-amino-5-(1-(3-(α-methoxyiminobenzyl)phenyl)ethyl)-1,2,4-oxadiazole (0.678 g, quantitive yield) as oily substance: NMR(CDCl3)δ1.70 (d, 3H), 3.97(s, 3H), 4.24(q, 1H), 4.48(broad singlet, 2H), 7.21-7.58(m, 9H) ppm; IR(neat) 3310, 3220, 1625, 1585, 1410, 1050 cm-1.

Workup

  1. temperatureAfter reflux
  2. extractionextracted with ethylacetate
  3. washThe extracts were washed with water
  4. customdried
  5. customanhydrous sodium sulfate, and evaporated under reduced pressure to a residue, which
  6. customwas chromatographed

Sources & evidence

ORD record
ord-3e837b4d55fc420abe5086578c328eb0
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

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