Sodium Hydroxide → HCID 86711948, compound

HRID 1475256Notes

Reaction equation

HRID 1475256 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][C:13]([C:15]([NH:17][NH2:18])=O)=[N:12][CH: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:14][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:11][N:12]=2)[N:24]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochlorideHCID 86711947HCID 86711947, compound

Product 1

HCID 86711948HCID 86711948, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(4-(trifluoromethoxy)phenyl)oxazole-2-carbohydrazide (4.6 g, 16 mmol), acetimidamide hydrochloride (2.27 g, 24 mmol) and NaOH (1.1 g, 27.2 mmol) in dry THF (100 mL) was stirred at reflux for 16 h. The mixture was then cooled to RT, concentrated under reduced pressure and the residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1 to 1:1) to afford the title compound as a yellow solid (4.0 g, 80%). MS (ES+) C13H9F3N4O2 requires: 310. found: 311 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.78 (d, J=9.0 Hz, 2H), 7.51 (s, 1H), 7.28 (d, J=9.0 Hz, 2H), 3.79 (s, 1H), 2.65 (s, 3H).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1 to 1:1)

Sources & evidence

ORD record
ord-7ff082b2d0d2464392badb45728c1ba3
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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