Ethylene Glycol → 3-Amino-5-(1-(3-(2-phenyl-1,3-dioxolan-2-yl)phenyl)ethyl)-1,2,4-oxadiazole

HRID 1646569Notes

Reaction equation

HRID 1646569 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:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)[CH3:8])[O:4][N:3]=1.[CH2:23](O)[CH2:24][OH:25]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=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]3([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[O:25][CH2:24][CH2:23][O:22]3)[CH:10]=2)[CH3:8])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 156760943-Amino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole

Product 1

HCID 156760963-Amino-5-(1-(3-(2-phenyl-1,3-dioxolan-2-yl)phenyl)ethyl)-1,2,4-oxadiazoleYield 77%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To 3-amino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole (1.20 g, 4.09 mmol) in toluene (10 ml) were added ethylene glycol (0.80 g, 12.9 mmol) and p-toluenesulfonic acid monohydrate (0.025 g, 0.15 mmol). After reflux for 10 h, the mixture was cooled at room temperature and extracted with toluene. The extracts were washed with aqueous sodium hydrogen carbonate and then water, dried with anhydrous sodium sulfate, and evaporated under reduced pressure to a residue, which was chromatographed to afford 3-amino-5-(1-(3-(2-phenyl-1,3-dioxolan-2-yl)phenyl)ethyl)-1,2,4-oxadiazole (1.06 g, 77% yield) as crystalline material: mp 112.0°-113.5° C.

Workup

  1. temperatureAfter reflux for 10 h
  2. extractionextracted with toluene
  3. washThe extracts were washed with aqueous sodium hydrogen carbonate
  4. dry with materialwater, dried with anhydrous sodium sulfate
  5. customevaporated under reduced pressure to a residue, which
  6. customwas chromatographed

Sources & evidence

ORD record
ord-d420630ed9ed487cb30a978abdae3a9c
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

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