Pyridine → 1-(Methylsulfonyl)-1H-benzotriazole

HRID 747568Notes

Reaction equation

HRID 747568 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1.N1C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][S:2]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178418385HCID 178418385, compound

Product 1

HCID 7920441-(Methylsulfonyl)-1H-benzotriazoleYield 96.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methanesulphonyl chloride (9.3 ml, 0.12 mol) in toluene (30 ml) was added dropwise to a solution of benzotriazole (11.9 g, 0.1 mol) and pyridine (12 ml, 0.16 mol) in toluene (120 ml). The reaction was stirred at room temperature for 20 h, diluted with ethyl acetate (150 ml), washed with water (2×100 ml), brine (150 ml) and dried (magnesium sulphate). The solvent was evaporated under vacuum to give 1-(methylsulphonyl)-1H-benzotriazole (19 g). NMR: ∂H CDCl3 8.17,(1H, m), 8.02,(1H, m), 7.69,(1H, m), 7.55,(1H, m), 3.52,(3H, s).

Workup

  1. washwashed with water (2×100 ml), brine (150 ml)
  2. dry with materialdried (magnesium sulphate)
  3. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-1b5fd5861ece48a585c6a5fc4575a7e4
Source dataset
uspto-grants-2008_07
Patent number
US07396843B2

Reaction notes

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