Pyridine → Ethyl 5-(4-methylphenyl)-1,3,4-oxadiazole-2-carboxylate

HRID 1035168Notes

Reaction equation

HRID 1035168 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][NH:9][C:10](=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:2]1([CH3:1])[CH:18]=[CH:17][C:5]([C:6]2[O:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 66653417HCID 66653417, compound

Product 1

HCID 58043111Ethyl 5-(4-methylphenyl)-1,3,4-oxadiazole-2-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6A (8.1 g, 32.4 mmol) was dissolved in toluene (200 ml) and pyridine (2.6 mL, 32.4 mmol). Thionyl chloride (9.6 g, 81 mmol) was added and the reaction was refluxed for 8 h. The solvent was evaporated and the residue was partitioned between DCM and aqueous NaHCO3 (sat.). The organic phase was further washed with 0.1 M HCl and aqueous NaHCO3 (sat.), filtered through a phase separator and the solvent was removed by evaporation. There was obtained 7.0 g (93%) of 6B as an off white solid. 1H NMR (400 MHz, CDCl3): δ 1.48 (t, 3H), 2.44 (s, 3H), 4.54 (q, 2H), 7.34 (d, 2H), 8.04 (d, 2H).

Workup

  1. temperaturethe reaction was refluxed for 8 h
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between DCM and aqueous NaHCO3 (sat.)
  4. washThe organic phase was further washed with 0.1 M HCl and aqueous NaHCO3 (sat.)
  5. filtrationfiltered through a phase separator
  6. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-e6c493c307a64a6396025f058697adbf
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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