Benzenesulfonyl chloride → 2-Benzenesulfonylamino-3-iodo-5-methylthiopyridine

HRID 1838312Notes

Reaction equation

HRID 1838312 reaction equation
[NH2:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([S:9][CH3:10])=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[C:16]1([S:22]([NH:1][C:2]2[C:7]([I:8])=[CH:6][C:5]([S:9][CH3:10])=[CH:4][N:3]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 154868502-Amino-3-iodo-5-methylthiopyridine

Product 1

HCID 154868512-Benzenesulfonylamino-3-iodo-5-methylthiopyridineYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-amino-3-iodo-5-methylthiopyridine (7.63 g) in pyridine (30 ml), benzenesulfonyl chloride (7.9 ml) was added at 15 to 30° C. under nitrogen atmosphere and the mixture was stirred at 60° C. for 15 hours. The reaction solution was then poured into a saturated aqueous sodium hydrogencarbonate solution, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. A solution of the resulting crude bis(benzenesulfonyl) product in a mixture of methanol/dioxane (1:1, 200 ml) was added a 1N aqueous potassium hydroxide solution (64 ml) at 15 to 30° C. and the mixture was stirred at 60° C. for 1 hour. The reaction solution was then poured into a saturated aqueous sodium hydrogencarbonate solution, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (methanol chloroform=1:50) to obtain 6.4 g (56%) of the desired product as a white powder.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionA solution of the resulting crude bis(benzenesulfonyl) product in a mixture of methanol/dioxane (1:1, 200 ml)
  6. additionwas added a 1N aqueous potassium hydroxide solution (64 ml) at 15 to 30° C.
  7. stirringthe mixture was stirred at 60° C. for 1 hour
  8. additionThe reaction solution was then poured into a saturated aqueous sodium hydrogencarbonate solution
  9. extractionextracted with dichloromethane
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting residue was separated

Sources & evidence

ORD record
ord-fe8b45c9298f4d10830679b155b9d0fe
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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