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

HRID 1372485Notes

Reaction equation

HRID 1372485 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[I:12][C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=1.CO>N1C=CC=CC=1>[I:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 73974-Toluenesulfonyl chlorideHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 21772024N-(5-Iodo-pyridin-2-YL)-4-methyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Toluenesulfonyl chloride (2.00 g, 10.4 mmol) was added to a solution of 5-iodo-2-aminopyridine (2.50 g, 11.4 mmol) in 6 mL of pyridine, and the resultant solution was warmed at 90° C. for 18 h. After cooling to room temperature, the solution was added portionwise to 75 mL of ice-water with stirring. The resultant precipitate was collected, washed with water, and dried in vacuo to afford a pale yellow powder, which was stirred with 20 mL of methanol for several minutes. The solid product was then collected, washed with methanol, and dried in vacuo to provide the title compound as an off-white powder. LC/MS 374.8 (M+1).

Workup

  1. customThe resultant precipitate was collected
  2. washwashed with water
  3. customdried in vacuo
  4. customto afford a pale yellow powder, which
  5. customThe solid product was then collected
  6. washwashed with methanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-082c0a7fcb6c40b98fc0d69b25098261
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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