Triethylamine → 5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one

HRID 856038Notes

Reaction equation

HRID 856038 reaction equation
C(N(CC)CC)C.[C:8](N1C=CN=C1)(N1C=CN=C1)=[O:9].[F:20][C:21]([F:34])([F:33])[O:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=1>C1COCC1>[F:20][C:21]([F:33])([F:34])[O:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]2[O:28][C:8](=[O:9])[NH:30][N:29]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27772304-(Trifluoromethoxy)benzoic acid hydrazide

Product 1

HCID 230813495-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-oneYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (3.52 ml, 25.28 mmol) and 1,1′-carbonyldiimidazole (4.84 g, 29.87 mmol) were added to a solution of 4-trifluoromethoxybenzoic hydrazide (5.06 g, 22.98 mmol) in THF (150 ml) while cooling in an ice-bath and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, to which water was added. The mixture was extracted with ethyl acetate, and the extract was dried over magnesium sulfate and then concentrated under reduced pressure to afford 5-(4-trifluoromethoxyphenyl)-3H-[1,3,4]oxadiazol-2-one (5.34 g, yield 94%) as a colorless crystalline powder.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to which water
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7344eb8b5604348905737af6d806895
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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