Sodium Acetate → 1-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol

HRID 732114Notes

Reaction equation

HRID 732114 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([O:7][N:8]=[C:9]([NH2:13])[CH:10]([OH:12])[CH3:11])=O.C([O-])(=O)C.[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:8]=[C:9]([CH:10]([OH:12])[CH3:11])[N:13]=2)[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 76579670N'-[(3-chlorobenzoyl)oxy]-2-hydroxypropanimidamide

Product 1

HCID 578379411-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanolYield 25.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

27.2 g crude N′-[(3-chlorobenzoyl)oxy]-2-hydroxypropanimidamide was dissolved in ethanol (250 mL) and refluxed for 1 h, followed by addition of 14.0 g (170 mmol) sodium acetate in water (40 mL). After refluxing o.n., cooling to r.t. and addition of water (250 mL) the mixture was concentrated in vacuo to about ½ of its volume, resulting in a precipitate which was filtered off and recrystallized from EA/Hep to yield 6.45 g (25%) of the title compound. 1H NMR: 8.14 (s, 1 H), 8.02 (d, 1 H), 7.57 (d, 1 H), 7.47 (t, 1 H), 5.04-5.14 (m, 1 H), 2.51 (d, 1 H), 1.67 (d, 3 H)

Workup

  1. temperaturerefluxed for 1 h
  2. temperatureAfter refluxing o.n
  3. concentrationwas concentrated in vacuo to about ½ of its volume
  4. customresulting in a precipitate which
  5. filtrationwas filtered off
  6. customrecrystallized from EA/Hep

Sources & evidence

ORD record
ord-e1a2e5d6709f4f4b8b088b3abbabb6eb
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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