Sodium hydride → HCID 90832871, compound

HRID 2216247Notes

Reaction equation

HRID 2216247 reaction equation
[N:1]1[C:5]2=[CH:6][CH:7]=[C:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:9][C:4]2=[N:3][N:2]=1.[H-].[Na+].[CH3:17][CH2:18][CH2:19]I>CN(C)C=O>[CH2:17]([N:2]1[N:1]=[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:4]2=[N:3]1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 69663982HCID 69663982, compound

Product 1

HCID 90832871HCID 90832871, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl 5-benzotriazoleacetate (10 g, 0.0523 mol) in N,N-dimethylformamide was added dropwise to a chilled (ice-bath) suspension of sodium hydride (60% dispersion in oil, 2.3 g, 0.0575 mol) in N,N-dimethylformamide. When the addition was complete, the ice-bath was removed and the mixture stirred for 1 hour. N-Propyl iodide (9.78 g, 0.0575 mol) was added dropwise, and once the addition was complete the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured onto ice/water, and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was further purified by column chromatography to afford methyl (2-propylbenzotriazol-5-yl)acetate (4.8 g).

Workup

  1. temperaturea chilled
  2. additionWhen the addition
  3. customthe ice-bath was removed
  4. additiononce the addition
  5. stirringwas stirred at room temperature for 3 hours
  6. additionThe reaction mixture was poured onto ice/water
  7. extractionextracted with ethyl acetate
  8. extractionThe organic extract
  9. washwas washed with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe filtrate evaporated in vacuo
  13. customThe residue was further purified by column chromatography

Sources & evidence

ORD record
ord-bcb88f4f386e4fe19d9042fe64fcb86d
Source dataset
uspto-grants-2006_09
Patent number
US07112553B1

Reaction notes

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