Triethylamine → (6-Chloropyridin-3-yl)methyl methanesulphonate
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:9][CH2:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:20])=[O:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (6-chloro-3-pyridyl)methanol (4.5 g, 31.3 mmol) and triethylamine (13.2 ml, 94.7 mmol) in dichloromethane (90 ml) was dropwise added methanesulfonyl chloride (3.6 ml, 46.5 mmol) over 45 minutes at −9° C. to 4° C. under an atmosphere of nitrogen gas, followed by stirring as it was. After 1 hour, the reaction mixture was elevated to room temperature. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and a saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate and concentrated, to give the title compound (6.14 g, 88%) as a pale brown solid.
Workup
- customover 45 minutes
- customat −9° C. to 4° C.
- customwas elevated to room temperature
- washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution
- dry with materiala saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c17b9e1d63354a7ead1b8e633c251f3c
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07396836B2
Reaction notes
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