Pyridine → N-(5-Iodo-pyridin-2-YL)-4-methyl-benzenesulfonamide

HRID 60380

Reaction equation

HRID 60380 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.N1C=CC=CC=1>O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:9])=[CH:11][CH:12]=2)(=[O:18])=[O:17])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 21772024N-(5-Iodo-pyridin-2-YL)-4-methyl-benzenesulfonamideYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-iodopyridin-2-amine (25.5 g), 4-methylbenzene-1-sulfonyl chloride (23.2 g) and pyridine (250 mL) was stirred at 100° C. overnight. The reaction mixture was poured into water (1.2 L) and stirred. The resulting solid was collected by filtration. The obtained solid was washed with water and diethyl ether and dried in vacuo to give the title compound (37.4 g) as a white solid.

Workup

  1. stirringstirred
  2. filtrationThe resulting solid was collected by filtration
  3. washThe obtained solid was washed with water and diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2f3fa683d20e43d580c697040c92e7b9
Source dataset
uspto-grants-2016_09
Patent number
US09440987B2

Linked notes

Loading…