4-Toluenesulfonyl chloride → N-{5-[(4-methoxybenzyl)oxy]pyridin-2-yl}-4-methylbenzenesulfonamide

HRID 2095832Notes

Reaction equation

HRID 2095832 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:18])=[CH:20][CH:21]=3)(=[O:27])=[O:26])=[N:13][CH:14]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 284910055-((4-Methoxybenzyl)oxy)pyridin-2-amine

Product 1

HCID 66968540N-{5-[(4-methoxybenzyl)oxy]pyridin-2-yl}-4-methylbenzenesulfonamideYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-[(4-methoxybenzyl)oxy]pyridin-2-amine (24 g, 104 mmol) in pyridine (210 mL) was added 4-methylbenzenesulfonyl chloride (20.9 g, 110 mmol) at 0° C., and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated, the residue was washed with saturated aqueous sodium hydrogen carbonate solution and ethyl acetate to give the title compound (37 g, 93%) as a pale-red solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with saturated aqueous sodium hydrogen carbonate solution and ethyl acetate

Sources & evidence

ORD record
ord-c7aaf62766c943bb8e585406c76afb44
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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