Pyridine → N-(2-methylphenyl)methanesulfonamide

HRID 607537Notes

Reaction equation

HRID 607537 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:16]([CH3:15])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7242O-ToluidineHCID 31297Methanesulfonyl chloride

Product 1

HCID 5065377N-(2-methylphenyl)methanesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of o-toluidine (1.07 ml, 10 mmol) and pyridine (0.86 ml, 10.6 mmol) in dichloromethane (2 mL) was added methanesulfonyl chloride (0.81 ml, 10.5 mmol) dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was quenched by 1 N HCl aqueous solution and extracted with EtOAc. The organic layer was concentrated in vacuo to afford the title compound (1.84 g, 10 mmol, quant.) as an orange solid.

Workup

  1. customThe reaction mixture was quenched by 1 N HCl aqueous solution
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-2cbe6db1bd2a4641a1240c8a988dbf66
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

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