Methanol → HCID 88365911, compound

HRID 1737215Notes

Reaction equation

HRID 1737215 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[N:13][OH:14])[CH3:12].[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[N:26]1[C:30](Cl)=[N:29][N:28]([CH3:32])[C:27]1=[O:33].[CH3:34][O-:35].[Na+].CO>O1CCCC1.C(OCC)(=O)C>[CH3:34][O:35][C:30]1[N:26]([C:20]2[C:19]([CH2:18][O:14][N:13]=[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[CH3:12])=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:25])[C:27](=[O:33])[N:28]([CH3:32])[N:29]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 24758Sodium hydrideHCID 31856651674-06-7HCID 10942334Sodium MethoxideHCID 218419724-[2-(bromomethyl)-6-methylphenyl]-5-chloro-2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one

Product 1

HCID 88365911HCID 88365911, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-naphthalenyl)ethanone oxime (492 mg, 2.65 mmol) in tetrahydrofuran (7.5 mL) cooled to 0° C. under a nitrogen atmosphere was added 95% NaH (69 mg, 2.88 mmol) and the mixture was stirred for 20 min. The title compound of Step E (700 mg, 2.21 mmol) was then added to the reaction and the mixture was stirred at room temperature for 3 h. Sodium methoxide as a 30% solution in methanol (1.3 mL, 6.63 mmol) was added and the reaction mixture was heated to reflux for 10 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated ammonium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (25% ethyl acetate in hexanes as eluent) to give 306 mg of the title compound of Step F, a compound of the invention, as a golden oil. 1H NMR (CDCl3): δ 2.19 (s,3H), 2.32 (s,3H), 3.41 (s,3H), 3.89 (s,3H), 5.21 (AB q,2H), 7.30 (d,1H), 7.36-7.5 (m,4H), 7.8 (m,4H), 7.97 (s,1H).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 h
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 10 h
  4. washwashed with saturated ammonium chloride
  5. dry with materialThe organic phase was dried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel (25% ethyl acetate in hexanes as eluent)

Sources & evidence

ORD record
ord-eba9c9ca04534a478b77d5dae7df4b53
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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