Hydrochloric Acid → HCID 13809948, compound

HRID 638566Notes

Reaction equation

HRID 638566 reaction equation
[C:1]([C:9]1[N:13]=[C:12]([CH2:14][C:15](N)=[O:16])[O:11][N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)(C)C>[CH:1]([O:8][C:15](=[O:16])[CH2:14][C:12]1[O:11][N:10]=[C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:13]=1)([CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13576493HCID 13576493, compound

Product 1

HCID 13809948HCID 13809948, compoundYield 185.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 9.2 g of (3-benzoyl-1,2,4-oxadiazol-5-yl)acetamide in 300 ml isopropanol was saturated with HCl gas. The resulting mixture was warmed to 70° and maintained there for 11 hours. The resulting cooled mixture was filtered and diluted with 400 ml water. Extraction with Et2O (3×300 ml), washing the organics with a saturated NaHCO3 solution, drying over MgSO4, filtration and concentration gave 10.1 g of an oil. Purification of 9.8 g of this oil by high pressure liquid chromatography with 20% hexane/CH2Cl2 used as an eluent gave 7.0 g (64%) of an oil.

Workup

  1. temperatureThe resulting mixture was warmed to 70°
  2. temperaturemaintained there for 11 hours
  3. temperatureThe resulting cooled mixture
  4. filtrationwas filtered
  5. additiondiluted with 400 ml water
  6. extractionExtraction with Et2O (3×300 ml)
  7. washwashing the organics with a saturated NaHCO3 solution
  8. dry with materialdrying over MgSO4, filtration and concentration

Sources & evidence

ORD record
ord-2012643c601e40ff8552d3cc2e2dbf35
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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