Ammonium Chloride → 5-Chloro-2-(cyclopropylsulfonyl)pyridine

HRID 1964723Notes

Reaction equation

HRID 1964723 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:11][CH2:12][CH2:13]Cl)(=[O:10])=[O:9])=[N:6][CH:7]=1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 661280795-Chloro-2-[(3-chloropropyl)sulfonyl]pyridine

Product 1

HCID 666814225-Chloro-2-(cyclopropylsulfonyl)pyridineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

5-Chloro-2-[(3-chloropropyl)sulfonyl]pyridine (732 mg, 3.05 mmol) synthesized in Example (125b) was dissolved in tetrahydrofuran (10 mL) and cooled to −30° C., and subsequently potassium-t-butoxide (582 mg, 5.18 mmol) was added, followed by stirring as it is for 30 minutes. To the reaction solution, a saturated aqueous ammonium chloride solution (40 mL) was added, and extraction was carried out twice with methylene chloride (40 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-25%) to afford the desired compound (397 mg, yield 60%).

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-25%)

Sources & evidence

ORD record
ord-fdef01d0816546919692b06efeeada45
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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