Triethylamine → 3-(1,2,3-Triazol-1-yl)propyl methanesulfonate

HRID 1506935Notes

Reaction equation

HRID 1506935 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][OH:9])[CH:5]=[CH:4][N:3]=[N:2]1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:9][CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[N:2]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 220309141-(3-Hydroxypropyl)-1,2,3-triazole

Product 1

HCID 866805493-(1,2,3-Triazol-1-yl)propyl methanesulfonateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(1,2,3-triazol-1-yl)propanol (2.5 g, 19.66 mmol) was dissolved in dichloromethane (50 mL), and the solution was cooled to 0° C. Then, triethylamine (5.53 mL, 39.32 mmol) and methane sulfonyl chloride (2.3 mL, 29.5 mmol) were added thereto. The reaction mixture was warmed to room temperature, stirred for 2 hours, extracted with dichloromethane and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford the title compound (3.01 g, 75%).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. extractionextracted with dichloromethane and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-7521691910cc4a899d01c0421784865d
Source dataset
uspto-grants-2015_12
Patent number
US09221790B2

Reaction notes

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