Hydroxyamine hydrochloride → 3-(alpha-Hydroxyiminopropyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole

HRID 4898Notes

Reaction equation

HRID 4898 reaction equation
[CH2:1]([C:3]([C:5]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[O:7][N:6]=1)=O)[CH3:2].Cl.[OH:21][NH2:22]>CO>[OH:21][N:22]=[C:3]([C:5]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[O:7][N:6]=1)[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 197971233-Ethylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole

Product 1

HCID 1363314963-(alpha-Hydroxyiminopropyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazoleYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.9 g of 3-ethylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole and 0.21 g of hydroxyamine hydrochloride were added to 10 ml of methanol. The mixture was heated to reflux for 4 hours. After evaporation of methanol, water was added to the residue. The aqueous solution was extracted with ethylacetate. After evaporation of ethylacetate, the residue was purified by column chromatography(benzene:ether=1.1) to provide 0.80 g of the desired product(yield: 85.0%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customAfter evaporation of methanol, water
  4. additionwas added to the residue
  5. extractionThe aqueous solution was extracted with ethylacetate
  6. customAfter evaporation of ethylacetate
  7. customthe residue was purified by column chromatography(benzene:ether=1.1)

Sources & evidence

ORD record
ord-ee847813e8e14c88ba9cb5b8597ec847
Source dataset
uspto-grants-1993_09
Patent number
US05242890

Reaction notes

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