Methane → 5-(4-Nitrophenyl)-3-(2-thienyl)-1,2,4-oxadiazole

HRID 2397861Notes

Reaction equation

HRID 2397861 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[N:8][OH:9])[NH2:7].[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=O)=[CH:15][CH:14]=1)([O-:12])=[O:11].C>O1CCOCC1.B(F)(F)F.C(OCC)C>[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17]2[O:9][N:8]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[N:7]=2)=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 297MethaneHCID 85024-Nitrobenzoyl chlorideHCID 2760620N'-Hydroxythiophene-2-carboximidamide

Product 1

HCID 7186945-(4-Nitrophenyl)-3-(2-thienyl)-1,2,4-oxadiazoleYield 65.3%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-thiopheneamidoxime (10 g, 0.07 mole) and p-nitrobenzoyl chloride (13 g, 0.07 mole) in 400 ml of dry dioxane, 1 ml of BF3 -ethyl ether is added and the mixture is heated to reflux for 16 hours. Evaporation of the solvent in vacuo gives a dark solid. It is decolorized by treating with Darco (CHCl3). The solvent is concentrated in vacuo and the product is crystallized from ethanol to give 12.5 g (65%) of product, m.p. 169°-171°.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 16 hours
  3. customEvaporation of the solvent in vacuo
  4. customgives a dark solid
  5. concentrationThe solvent is concentrated in vacuo
  6. customthe product is crystallized from ethanol

Sources & evidence

ORD record
ord-db428f4d2dbf451dae2d96aadf338ff3
Source dataset
uspto-grants-1977_05
Patent number
US04022901

Reaction notes

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