Sodium hydride → HCID 10899425, compound

HRID 1780906Notes

Reaction equation

HRID 1780906 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[N:4]1.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:3]2[CH:7]=[CH:6][N:5]=[N:4]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 178418936HCID 178418936, compound

Product 1

HCID 10899425HCID 10899425, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 3.5 g (0.139 mol) of sodium hydride in 120 mL of DMF at 0° C. was added 8 g (0.115 mol) of 1,2,3-triazole in 50 mL of DMF dropwise, and the mixture was allowed to warm to room temperature and stirred for 1 h. The above mixture was cooled to 0° C., and 21.8 g (0.139 mol) of p-methoxybenzyl chloride was added, and the mixture was allowed to warm to room temperature and stirred for 20 h. The reaction mixture was concentrated in vacuo and the residue was purified by chromatography on silica (hexane/ethyl acetate) to afford 14 g (64.5%) of 1-(p-methoxybenzyl)-1,2,3-triazole.

Workup

  1. temperatureThe above mixture was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 20 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-aa8346898c194446b65096a59802d62f
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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