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

HRID 1672848Notes

Reaction equation

HRID 1672848 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([NH:9][NH2:10])=[O:8])([O-:3])=[O:2].[C:14](N1C=CN=C1)(N1C=CN=C1)=[O:15].Cl.O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]2[O:8][C:14](=[O:15])[NH:10][N:9]=2)[CH:11]=[CH:12][CH:13]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 32914983-Nitrobenzohydrazide

Product 1

HCID 127772575-(3-Nitrophenyl)-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Nitrobenzohydrazide (2.05 g, 11.3 mmol) obtained in Step 1 was dissolved in THF (57 mL), and the mixture was stirred at room temperature for 40 minutes after adding 1,1′-carbonyldiimidazole (2.01 g, 12.4 mmol). The mixture was stirred after adding 6 mol/L hydrochloric acid (40 mL) and water (20 mL), and the precipitated solid was filtered off and dried to give 5-(3-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one as a white solid. 5-(3-Nitrophenyl)-1,3,4-oxadiazol-2(3H)-one so obtained was dissolved in DMF (52 mL), and the mixture was stirred at room temperature for 40 minutes after adding potassium carbonate (2.14 g, 15.5 mmol) and methyl iodide (0.77 mL, 12.3 mmol). The mixture was stirred after adding water, and the precipitated solid was filtered off and dried to give 3-methyl-5-(3-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one (2.17 g, 87%).

Workup

  1. stirringThe mixture was stirred
  2. filtrationthe precipitated solid was filtered off
  3. customdried

Sources & evidence

ORD record
ord-f56649b048514010a4dde8dc7829db1d
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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