Pyridine → N-(5-fluoro-2-methylphenyl)methanesulfonamide

HRID 1438392Notes

Reaction equation

HRID 1438392 reaction equation
[N:1]1C=CC=CC=1.[F:7][C:8]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:9]=1N.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[F:7][C:8]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([NH:1][S:17]([CH3:16])(=[O:19])=[O:18])[CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 2629702-Fluoro-5-methylaniline

Product 1

HCID 6466945N-(5-fluoro-2-methylphenyl)methanesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a pyridine (20 ml) and DCM (40 ml) solution of 2-fluoro-5-methylaniline (purchased from ACROS, 3.5 g, 28 mmol), methanesulfonyl chloride (purchased from WAKO, 4.3 ml, 56 mmol) was added at room temperature and the mixture was stirred for 20 hours. The reaction was quenched with 2M sodium hydroxide aqueous solution and the aqueous layer was separated and washed with DCM. The layer was cooled to 0° C. and acidified to pH 2.0 using 2M HCl aqueous solution. The precipitates were collected, and the solvent evaporated in vacuo, to give the title compound (5.1 g, 90%). MS (ESI) m/z 202 (M−H)−

Workup

  1. customThe reaction was quenched with 2M sodium hydroxide aqueous solution
  2. customthe aqueous layer was separated
  3. washwashed with DCM
  4. customThe precipitates were collected
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-ce66f38c26b3444e811a400735804af0
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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