Ethyl orthoformate → 3-(4-Nitrophenyl)-1,2,4-oxadiazole

HRID 1665618Notes

Reaction equation

HRID 1665618 reaction equation
[CH:1](OCC)(OCC)OCC.[OH:11][NH:12][C:13](=[NH:23])[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1>C1COCC1>[N+:20]([C:17]1[CH:16]=[CH:15][C:14]([C:13]2[N:23]=[CH:1][O:11][N:12]=2)=[CH:19][CH:18]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 178513348HCID 178513348, compound

Product 1

HCID 27982883-(4-Nitrophenyl)-1,2,4-oxadiazoleYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triethyl orthoformate (2.93 g, 19.8 mmol) was added to a stirred solution of N-hydroxy-4-nitro-benzamidine (1.2 g, 6.6 mmol) in THF (15 mL). The mixture was cooled to 0° C. and boron triflouride dimethyl ether (900 mg, 7.9 mmol) was added drop wise. The mixture was maintained at room temperature for three hours. The volatiles were evaporated and the residue was washed with ether and dried to afford 650 mg (55%) of 3-(4-nitro-phenyl)-[1,2,4]oxadiazole.

Workup

  1. temperatureThe mixture was maintained at room temperature for three hours
  2. customThe volatiles were evaporated
  3. washthe residue was washed with ether
  4. customdried

Sources & evidence

ORD record
ord-f152925894374548be7a82e0028f655e
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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