Sodium Hydroxide → HCID 86711953, compound

HRID 1475263Notes

Reaction equation

HRID 1475263 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([C:15]([NH:17][NH2:18])=O)[O:12][N:11]=2)=[CH:6][CH:5]=1.Cl.[C:22](=N)([NH2:24])[CH3:23].[OH-].[Na+]>C1COCC1>[CH3:23][C:22]1[NH:18][N:17]=[C:15]([C:13]2[O:12][N: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)[CH:14]=2)[N:24]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochlorideHCID 86711954HCID 86711954, compound

Product 1

HCID 86711953HCID 86711953, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(4-(trifluoromethoxy)phenyl)isoxazole-5-carbohydrazide (2.4 g, 8.5 mmol) and acetimidamide hydrochloride (1.2 g, 12.8 mmol) in dry THF (60 mL), was added NaOH (512 mg, 12.8 mmol). The mixture was then refluxed for 16 h, then cooled to RT and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the title compound as a white solid (1.9 g, 71%). 1H NMR (500 MHz, DMSO-d6) δ 8.12 (d, J=7.2 Hz, 2H), 7.58 (s, 1H). 7.54 (d, J=6.4 Hz, 2H), 2.46 (s, 3H). MS (ES+) C13H9F3N4O2 requires: 310. found: 311 [M+H]+.

Workup

  1. temperatureThe mixture was then refluxed for 16 h
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-462d331df76a441ead83668d0ae2ee97
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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