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

HRID 2202831Notes

Reaction equation

HRID 2202831 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 heated at 100° C. overnight. The mixture was poured into water (1.2 L) with stirring, and the resulting precipitate was collected by filtration. The solid was washed with water and Et2O successively, and dried in vacuo to give the title compound (37.4 g) as a white solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washThe solid was washed with water and Et2O successively
  3. customdried in vacuo

Sources & evidence

ORD record
ord-422f574d8bea46a58baca58f1cde2d9c
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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