Triethylamine → N-[[2-(4-Methoxybenzyl)-2H-[1,2,4]triazol-3-yl]methyl]methylamine

HRID 17431Notes

Reaction equation

HRID 17431 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13]O)=[N:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1.[CH2:17]([N:19](CC)CC)C.CS(Cl)(=O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][NH:19][CH3:17])=[N:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10775239(1-(4-Methoxybenzyl)-1H-1,2,4-triazol-5-yl)methanol

Product 1

HCID 59715895N-[[2-(4-Methoxybenzyl)-2H-[1,2,4]triazol-3-yl]methyl]methylamineYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(4-Methoxybenzyl)-2H-[1,2,4]triazol-3-yl]methanol (0.50 g, 2.28 mmol) was dissolved in dichloromethane (10 ml), then triethylamine (0.36 ml, 2.60 mmol) was added. With cooling with ice, methanesulfonyl chloride (0.20 ml, 2.58 mmol) was added, followed by stirring at room temperature for 2 hours. The reaction liquid was concentrated, ethyl acetate was added, followed by washing. After drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (25 ml), then aqueous methylamine solution (40%, 5 ml) was added. After stirring at room temperature for 3 days, the reaction liquid was concentrated. This was diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain a pale yellow oil (0.44 g, 83%).

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. concentrationwas concentrated
  4. additionethyl acetate was added
  5. washby washing
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. dissolutionthe resulting residue was dissolved in tetrahydrofuran (25 ml)
  9. additionaqueous methylamine solution (40%, 5 ml) was added
  10. stirringAfter stirring at room temperature for 3 days
  11. customthe reaction liquid
  12. concentrationwas concentrated
  13. additionThis was diluted with ethyl acetate
  14. washwashed with water
  15. dry with materialdried over anhydrous sodium sulfate
  16. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-aef99694bce04a5ca74c422b290bbab7
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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