Triethylamine → (1-Methyl-1H-1,2,4-triazol-5-yl)methyl methanesulfonate

HRID 1169690Notes

Reaction equation

HRID 1169690 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[N:5][CH:4]=[N:3]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:8][CH2:7][C:6]1[N:2]([CH3:1])[N:3]=[CH:4][N:5]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanol

Product 1

HCID 86611705(1-Methyl-1H-1,2,4-triazol-5-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-methyl-1H-1,2,4-triazol-5-yl)methanol (53 mg, 0.47 mmol) in 2 mL of dichloromethane was added triethylamine (0.13 mL, 0.94 mmol), followed by methanesulfonyl chloride (0.044 mL, 0.56 mmol). The mixture was stirred at room temperature for 3 hours, then partitioned between EtOAc and water. The organic layer was washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the title product. ESI+MS: 192.2 [M+H]+.

Workup

  1. custompartitioned between EtOAc and water
  2. washThe organic layer was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3be42d30239c49a0a84b2c38aaeb997a
Source dataset
uspto-grants-2010_11
Patent number
US07825131B2

Reaction notes

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