Sodium hydride → HCID 18510254, compound

HRID 1371048Notes

Reaction equation

HRID 1371048 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])=[CH:9][CH:8]=2)[O:4][N:3]=1.[H-].[Na+].[CH2:24](Br)[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([CH2:24]/[CH:25]=[CH:26]/[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])=[CH:11][CH:12]=2)[O:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 18510213HCID 18510213, compound

Product 1

HCID 18510254HCID 18510254, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-1-phenyl 1-ethanone (0.2 g, 0.72 mmole) in DMF (3 mL) was added NaH (0.022 g, 0.7 mmole) at 0° C. The reaction was stirred for 15 min. Then a solution of cinnamyl bromide (0.16 g, 0.84 mmol) in 1 mL DMF was added. The reaction was warmed to room temperature, and was then quenched with saturated NH4Cl solution and extracted with ethyl acetate. The organic phase was then dried (Na2SO4), filtered, and evaporated to give the title compound.

Workup

  1. customwas then quenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was then dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3197a6f1842340548a93e02dbc9f31c8
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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