Triethylamine → N-(6-Chloro-2-methylpyridin-3-yl)-N-(methylsulfonyl)methanesulfonamide

HRID 386027Notes

Reaction equation

HRID 386027 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N:9]([S:18]([CH3:17])(=[O:20])=[O:19])[S:18]([CH3:17])(=[O:20])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70095003-Amino-6-chloro-2-picoline

Product 1

HCID 59526403N-(6-Chloro-2-methylpyridin-3-yl)-N-(methylsulfonyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a dry flask, 6-chloro-2-methylpyridin-3-amine (160 mg, 1.12 mmol) and triethylamine (470 μl, 3.37 mmol) were taken up in dichloromethane (5.6 ml) under argon. The solution was cooled to 0° C. and stirred for 20 minutes. Methanesulfonyl chloride (131 μl, 1.68 mmol) was added dropwise over 15 minutes. The mixture was allowed to warm to room temperature and stirred as such for 16 hours. The reaction was quenched with aqueous sodium bicarbonate and washed three times with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated to afford the title compound.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred as such for 16 hours
  3. customThe reaction was quenched with aqueous sodium bicarbonate
  4. washwashed three times with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aef7ba9d803140e68f6e191b7bf3c5d6
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…