4-Chlorobenzonitrile → Ethyl 5-(4-chlorophenyl)-[1,2,4]oxadiazole-3-carboxylate

HRID 1419699Notes

Reaction equation

HRID 1419699 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[N+:10]([CH:13](C(OCC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])([O-])=[O:11]>CCCCCCCCCCCC>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[O:11][N:10]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:7]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 121634-ChlorobenzonitrileHCID 97657Diethyl nitromalonate

Product 1

HCID 54161468Ethyl 5-(4-chlorophenyl)-[1,2,4]oxadiazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8182DodecaneSolvent

Conditions

Temperature
150 °C

Procedure

This product was prepared by a modification of the general procedure described in Shimizu, T. et al. Bull.Chem.Soc.Jpn. 1985, 58, 2519. A mixture of 4-chlorobenzonitrile (1.7 g, 12.2 mmol), and diethyl nitromalonate (2.5 g, 12.2 mmol) in dodecane (20 mL) was heated at 150° C. for 15 h. After the reaction was complete, the mixture was allowed to cool to room temperature and was then concentrated in vacuo. The residue was purified by flash chromatography to yield ethyl 5-(4-chlorophenyl)-1,2,4-oxadiazole-3-carboxylate as a light brown solid: mp 88°-89° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.15 (dt, Jt =2.3, Jd =8.7, 2H, arom), 7.54 (dt, Jt =2.3, Jd =8.7, 2H, arom), 4.55 (q, J=7.1, 2H, OCH2), 1.47 (t, J=7.1, 3H, OCH2CH3).

Workup

  1. customThis product was prepared by a modification of the general procedure
  2. temperatureto cool to room temperature
  3. concentrationwas then concentrated in vacuo
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-dbab2c55bea244c6bfcd780324872721
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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