2-Aminopyridine → 6-Aminopyridine-3-sulfonyl chloride

HRID 989253Notes

Reaction equation

HRID 989253 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>>[NH2:6][C:7]1[N:8]=[CH:9][C:10]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 104392-AminopyridineHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 121090746-Aminopyridine-3-sulfonyl chlorideYield 32.2%

Conditions

Temperature
150 °C

Procedure

To 123.8 g (1.06 mol) of chlorosulfonic acid was added 10.00 g (0.106 mol) of 2-aminopyridine by portions under ice-cooling. Thionyl chloride (50.56 g, 0.425 mol) was added thereto, followed by heating under reflux for 2.5 hours and further stirring at 150° C. for 7 hours. The reaction solution was poured onto ice water, neutralized by adding sodium bicarbonate thereto and extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution, water and brine successively, dried over magnesium sulfate and then concentrated to dryness. The resulting residue was suspended in ethyl ether and the insoluble matters were filtered off. The filtrate was concentrated to dryness and the resulting residue was recrystallized from ethyl ether-hexane to give 6.58 g of the title compound.

Workup

  1. temperaturecooling
  2. temperatureby heating
  3. temperatureunder reflux for 2.5 hours
  4. additionThe reaction solution was poured onto ice water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with a saturated sodium bicarbonate solution, water and brine successively
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated to dryness
  9. filtrationthe insoluble matters were filtered off
  10. concentrationThe filtrate was concentrated to dryness
  11. customthe resulting residue was recrystallized from ethyl ether-hexane

Sources & evidence

ORD record
ord-c6455f8d0f6f4ccf8cf079ffeff22a4c
Source dataset
uspto-grants-2003_10
Patent number
US06638964B2

Reaction notes

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