Hydrochloric Acid → 3-Phenyl-1,2,4-oxadiazol-5(4H)-one

HRID 2263358Notes

Reaction equation

HRID 2263358 reaction equation
C([O:3][C:4]([O:6][N:7]=[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:9])=O)C.[OH-].[Na+].Cl>O.C(O)C>[C:10]1([C:8]2[NH:9][C:4](=[O:3])[O:6][N:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71364520N'-[(Ethoxycarbonyl)oxy]benzenecarboximidamide

Product 1

HCID 1354185773-Phenyl-1,2,4-oxadiazol-5(4H)-oneYield 53.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of N′-[(ethoxycarbonyl)oxy]benzenecarboximidamide (17.0 g, 81.6 mmol) and sodium hydroxide (6.28 g, 157 mmol) in water (380 ml) and ethanol (95 ml) was stirred at room temperature for 3 hours. Thereto 1 N hydrochloric acid (157 ml) was added, and a precipitated solid was collected by filtration and washed with water to give 7.05 g (53.4%) of the desired product.

Workup

  1. filtrationa precipitated solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-5d40332b80c545f8a2d9be9b64866a0e
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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