Chloroform → Furo[2,3-b]pyridine-2-sulfonamide

HRID 1383016Notes

Reaction equation

HRID 1383016 reaction equation
[S:1]([C:5]1[O:16][C:8]2=[N:9][CH:10]=[C:11](C(O)=O)[CH:12]=[C:7]2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].C(Cl)(Cl)Cl.[OH-].[Na+]>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[S:1]([C:5]1[O:16][C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 14372169HCID 14372169, compound

Product 1

HCID 14372170Furo[2,3-b]pyridine-2-sulfonamideYield 42%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
225 °C

Procedure

A suspension of 2-sulfamoylfuro[2,3-b]pyridine-5-carboxylic acid (726 mg, 3.0 mmol) in quinoline (5 mL) containing copper dust (0.5 g) was heated under a nitrogen atmosphere at 225° C. for 3.5 hours. After cooling the reaction mixture to room temperature, chloroform and dilute sodium hydroxide solution were added. This biphasic mixture was filtered through a filter aid pad to remove black suspended material and then the basic aqueous layer was separated and acidified with conc. hydrochloric acid. The product was extracted into ethyl acetate which was dried over anhydrous sodium sulfate and filtered through a pad of charcoal. The residue obtained after removal of the solvent in vacuo was triturated with diethyl ether to give crude product (291 mg). This material was recrystallized from ethyl acetate to give pure product (250 mg, 42% yield), mp: 222°-223° C.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. filtrationThis biphasic mixture was filtered through a filter aid pad
  3. customto remove black suspended material
  4. customthe basic aqueous layer was separated
  5. extractionThe product was extracted into ethyl acetate which
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered through a pad of charcoal
  8. customThe residue obtained
  9. customafter removal of the solvent in vacuo
  10. customwas triturated with diethyl ether
  11. customto give crude product (291 mg)
  12. customThis material was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fc54b13252a741a8bb00cfedce7525a4
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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