Sodium Hydroxide → HCID 178434567, compound

HRID 1475269Notes

Reaction equation

HRID 1475269 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]([NH:17][NH2:18])=O)[CH:11]=2)=[CH:6][CH:5]=1.Cl.[C:22](=N)([NH2:24])[CH3:23].[OH-].[Na+]>C1COCC1>[CH3:23][C:22]1[N:24]=[C:15]([C:12]2[CH:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:20])([F:19])[F:1])=[CH:5][CH:6]=3)[O:14][N:13]=2)[NH:17][N:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochlorideHCID 86711960HCID 86711960, compound

Product 1

HCID 178434567HCID 178434567, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-(trifluoromethoxy)phenyl)isoxazole-3-carbohydrazide (4.4 g, 15.3 mmol) and acetimidamide hydrochloride (2.2 g, 23.0 mmol) in dry THF (100 mL) was added NaOH (920 mg, 23.0 mmol), and the resulting mixture was refluxed for 16 h. The solution was then cooled to RT and concentrated under reduced pressure, the residue was partitioned between H2O (80 mL) and EtOAc (2×100 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Petroleum ether:EtOAc=1:2) to afford the title compound as a yellow solid (2.1 g, 44.3%). MS (ES+) C13H9F3N4O2 requires: 310. found: 311 [M+H]+.

Workup

  1. temperaturethe resulting mixture was refluxed for 16 h
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was partitioned between H2O (80 mL) and EtOAc (2×100 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (Petroleum ether:EtOAc=1:2)

Sources & evidence

ORD record
ord-2ae841196587422ea9920767481b81c8
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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