4-Toluenesulfonyl chloride → N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide

HRID 1971614Notes

Reaction equation

HRID 1971614 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 57607460N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamideYield 100.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

2-amino-5-fluoropyridine (25 g, 0.22 mol) in pyridine (100 mL) was treated portion wise with p-toluenesulfonyl chloride (47.5 g, 0.25 mol) and heated at 80° C. for 2 hours. The cooled material was concentrated to remove the majority of pyridine. The resulting viscous solution was diluted with 200 ml of ethyl acetate then 200 ml of water. The resulting suspension was stirred for about an hour to break up the solids then filtered. The filter cake was washed with water then cold ethyl acetate, dried to afford 59 g of a light brown solid. Rf 0.43, 50% ethyl acetate/hexanes; MS m/z 266 (M+H).

Workup

  1. concentrationThe cooled material was concentrated
  2. customto remove the majority of pyridine
  3. additionThe resulting viscous solution was diluted with 200 ml of ethyl acetate
  4. filtrationthen filtered
  5. washThe filter cake was washed with water
  6. dry with materialcold ethyl acetate, dried

Sources & evidence

ORD record
ord-d04c216bbf2045dd911ad9b790b2ff3d
Source dataset
uspto-grants-2013_04
Patent number
US08431608B2

Reaction notes

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