Sodium hydride → 1-(2-Pentynyl)-3-(4-chlorophenyl)-1,2,4-triazin-6-one

HRID 1726924Notes

Reaction equation

HRID 1726924 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11](=[O:14])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:18][C:19]#[C:20][CH2:21][CH3:22]>CN(C=O)C>[CH2:18]([N:10]1[C:11](=[O:14])[CH:12]=[N:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:9]1)[C:19]#[C:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 897641-Chloro-2-pentyneHCID 202340913-(4-Chlorophenyl)-1,6-dihydro-1,2,4-triazin-6-one

Product 1

HCID 689609761-(2-Pentynyl)-3-(4-chlorophenyl)-1,2,4-triazin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 0.4 g of 3-(4-chlorophenyl)-1,2,4-triazin-6-one (1.9 mmol) was placed in 10 mL of DMF and cooled in an ice bath. Sodium hydride (NaH) (0.8 g of 60% dispersion, 2 mmol) was added, and the reaction mixture was held for 15 minutes. Excess 1-chloro-2-pentyne was added, the bath was removed, and the reaction mixture was allowed to warm to room temperature. Water and ethyl acetate were added. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and stripped. The crude product was chromatographed on silica gel to give 0.05 g of 1-(2-pentynyl)-3-(4-chlorophenyl)-1,2,4-triazin-6-one.

Workup

  1. temperaturecooled in an ice bath
  2. customthe bath was removed
  3. additionWater and ethyl acetate were added
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-e32c04f58e524b8791d4f73c5b57c329
Source dataset
uspto-grants-2009_02
Patent number
US07494996B2

Reaction notes

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