Potassium Carbonate → N'-benzyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide

HRID 1475193Notes

Reaction equation

HRID 1475193 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([C:15]([O:17]CC)=O)[O:12][N:11]=2)=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl.[CH2:30]([NH:37][NH2:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:30]([NH:37][NH:38][C:15]([C:13]1[O:12][N:11]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:9][CH:8]=2)[N:14]=1)=[O:17])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 146540Benzylhydrazine dihydrochlorideHCID 86711474HCID 86711474, compound2×

Product 1

HCID 86711886N'-benzyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazideYield 40.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of ethyl 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxylate (Intermediate A) (1.0 g, 3.3 mmol) and K2CO3 (1.1 g, 13 mmol) in THF (17 mL) was added benzylhydrazine dihydrochloride (780 mg, 5.0 mmol). The mixture was heated to 70° C. for 3 h. The mixture was cooled to RT, filtered (Celite), and concentrated under reduced pressure. The crude oil was purified by Biotage (5% EtOAc/Hexane—60% EtOAc) to provide a white solid (500 mg, 40%): MS (ES+) C17H13F3N4O3 requires: 378. found: 379 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered (Celite)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude oil was purified by Biotage (5% EtOAc/Hexane—60% EtOAc)

Sources & evidence

ORD record
ord-25e832fad5c34ebe81454731e4c91f05
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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