Benzoyl chloride, 3-nitro- → 3-(2,6-Dichlorophenyl)-5-(3-nitrophenyl)-1,2,4-oxadiazole

HRID 860397Notes

Reaction equation

HRID 860397 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:3]=1[C:4](=[N:6][OH:7])[NH2:5].[N+:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=O)([O-:15])=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:3]=1[C:4]1[N:5]=[C:19]([C:18]2[CH:22]=[CH:23][CH:24]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=2)[O:7][N:6]=1

Participants

5

Reactant 3

HCID 8495Benzoyl chloride, 3-nitro-HCID 10340Sodium CarbonateHCID 319562,6-dichloro-N'-hydroxybenzene-1-carboximidamide

Product 1

HCID 113596083-(2,6-Dichlorophenyl)-5-(3-nitrophenyl)-1,2,4-oxadiazoleYield 42.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,6-Dichlorobenzamidoxime (1.0 g) was dissolved in pyridine and m-nitrobenzoyl chloride (0.91 gm, 1.0 molar equivalent) was added. The solution was stirred at room temperature for 1 h under nitrogen, then heated at 90° C. for 4 h. The solution was cooled to room temperature, and poured into ice water. The pH of the solution was adjusted to approximately pH 10 with 2M aqueous sodium carbonate solution. The mixture was extracted with ether and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to dryness. The residue was dissolved in ethyl acetate. Addition of hexanes to the solution gave 3-(2,6-dichlorophenyl)-5-(3-nitrophenyl)-1,2,4-oxadiazole as a white solid (0.69 g). NMR (300 MHz, DMSO-d6): 8.52 (s, 1H), 8.38 (d, 1H), 8.18 (d, 1H), 7.78 (t, 1H), 7.57 ppm (m, 3H). LC-MS tr=38.2 min (Method W) MH++NA =359

Workup

  1. temperatureheated at 90° C. for 4 h
  2. temperatureThe solution was cooled to room temperature
  3. extractionThe mixture was extracted with ether
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to dryness
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. additionAddition of hexanes to the solution

Sources & evidence

ORD record
ord-819fbbfceb4b447e880e33cbc297cf44
Source dataset
uspto-grants-2006_12
Patent number
US07153880B2

Reaction notes

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