4-Toluenesulfonyl chloride → HCID 178427411, compound

HRID 1162446Notes

Reaction equation

HRID 1162446 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=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>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[N:8][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[NH:6][CH:7]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 178427411HCID 178427411, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 5-bromopyridin-2-amine (10.4 g, 60 mmol, Aldrich, St. Louis, Mo.) in pyridine (50 mL) was added p-toluenesulfonyl chloride (13 g, 66 mmol). The mixture was heated to 85° C. for 12 h. The solvent was removed under reduced pressure and the residue was taken up in 1 L of water and stirred for 1.5 h. The solid was collected by filtration and recrystallized from EtOAc to afford N-(5-bromopyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide (11.3 g, 57% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.23 (s, 1H), 8.27 (d, J=2.5 Hz, 1H), 7.89 (dd, J=8.8 Hz, 2.4 Hz, 1H), 7.79 (d, J=8.2 Hz, 2H), 7.37 (d, J=8.2 Hz, 2H), 7.03 (d, J=8.8 Hz, 1H), 2.35 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe solid was collected by filtration
  3. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-22e29a78c64a44c489028d175f38da40
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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