Triethylamine → 5-(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)pentyl methanesulfonate

HRID 550534Notes

Reaction equation

HRID 550534 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:4]=[C:3]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:3]1[N:2]([CH3:1])[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:4]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576918515-(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)-1-pentanol

Product 1

HCID 576919485-(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)pentyl methanesulfonateYield 116%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)-1-pentanol (127 mg, 0.52 mmol) in DCM (5 ml) was added trietylamine (0.62 mmol) and methansulfonyl chloride (0.57 mmol). The solution was stirred at r.t. for 2 h and quenched with saturated NaHCO3. The organic layer was dried over Na2SO4 and concentrated to give the title compound as light yellow oil (195 mg). MS (m/z): 324[MH]+.

Workup

  1. customquenched with saturated NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5f3d0708debc4e04907a62c187d9e063
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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