Sodium hydride → HCID 73848365, compound

HRID 1737208Notes

Reaction equation

HRID 1737208 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]=[CH:21][C:20]=1[N:25]1[C:29]([O:30][CH3:31])=[N:28][N:27]([CH3:32])[C:26]1=[O:33]>CN(C=O)C>[CH3:31][O:30][C:29]1[N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][O:14][N:13]=[C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH3:12])[C:26](=[O:33])[N:27]([CH3:32])[N:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31856651674-06-7HCID 110338324-[2-(Bromomethyl)phenyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

Product 1

HCID 73848365HCID 73848365, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.56 g (3.02 mmol) of 1-(2-naphthalenyl)ethanone oxime in 10 mL of DMF was added 0.13 g (3.28 mmol) of NaH. 0.75 (2.52 mmol) of the title compound of Step D was then added to the reaction and the mixture was stirred at room temperature for 3 h. The reaction mixture was washed successively with water and saturated NaCl and then extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel using 60% ethyl acetate/hexane as eluent to give 0.80 g (79% yield) of the title compound of Step E, a compound of the invention, as a solid melting at 91-94° C.

Workup

  1. washThe reaction mixture was washed successively with water and saturated NaCl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel using 60% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-bfa59fe4836a4827a5efe68e2fc92c2b
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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