Triethylamine → 3-(2-Pyridyl)-5-(3-cyano-5-nitrophenyl)-1,2,4-oxadiazole

HRID 431916

Reaction equation

HRID 431916 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6](Cl)=[O:7])#[N:2].[C:15]([C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([N+:26]([O-])=O)C=1)C(O)=O)#[N:16].C([N:31](CC)CC)C>ClCCl>[N:26]1[CH:24]=[CH:23][CH:19]=[CH:18][C:17]=1[C:15]1[N:16]=[C:6]([C:5]2[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[O:7][N:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219424583-Cyano-5-nitrobenzoyl chlorideHCID 219425653-Cyano-5-nitrobenzoic acid

Product 1

HCID 219425113-(2-Pyridyl)-5-(3-cyano-5-nitrophenyl)-1,2,4-oxadiazoleYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the general procedure for the preparation of acid chlorides, 3-cyano-5-nitrobenzoyl chloride was prepared from 3-cyano-5-nitrobenzoic acid (1.0 g, 5.1 mmol). A solution of the acid chloride in dichloromethane (5 mL) at 0° C. was treated with pyrid-2-ylamidoxime (700 mg, 5.1 mMol) and triethylamine (2.1 mL, 15.3 mmol) and then stirred at ambient temperature for 1 hour. The reaction mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was dissolved in N,N-dimethylformamide (5 mL) and heated at 110° C. for 4 hours. Standard work up and silica gel chromatography using hexanes:ethyl acetate:dichloromethane (3.5:0.5:4) afforded 149 mg (50%) of 3-(2-pyridyl)-5-(3-cyano-5-nitrophenyl)-1,2,4-oxadiazole: 1H NMR (CDCl3), 6 (ppm): 9.35 (d, 1H), 8.91 (s, 1H), 8.89 (d, 1H), 8.75 (s,1H), 8.26 (d, 1H), 7.94 (m, 1H), 7.53 (m, 1H).

Workup

  1. washThe reaction mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in N,N-dimethylformamide (5 mL)
  6. temperatureheated at 110° C. for 4 hours

Sources & evidence

ORD record
ord-c4d9b666254e46b88ed6319747e65c2d
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Linked notes

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