Hydrazine hydrate (1:1) → 3-(4-(Trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide

HRID 1475183Notes

Reaction equation

HRID 1475183 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](OCC)=[O:16])[O:12][N:11]=2)=[CH:6][CH:5]=1.[NH2:22][NH2:23].O>CCO>[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]([NH:22][NH2:23])=[O:16])[O:12][N:11]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86711474HCID 86711474, compound

Product 1

HCID 27446353-(4-(Trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazideYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of ethyl 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxylate (13.6 g, 45.0 mmol) in EtOH (200 mL), NH2NH2.H2O (80%, 14 mL, 225 mmol) was added. The reaction mixture was stirred at RT overnight. The desired compound precipitated from the reaction mixture, filtered and washed with EtOH (50 mL) to afford 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide as a light yellow solid (9.7 g, 75%). MS (ES+) C10H7F3N4O3 requires: 288. found: 289 [M+H]+.

Workup

  1. customThe desired compound precipitated from the reaction mixture
  2. filtrationfiltered
  3. washwashed with EtOH (50 mL)

Sources & evidence

ORD record
ord-12b83a742fb14b70b555ae86a03a95b7
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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