hydroxylamine-O-sulfonic acid → 7-Methylfuro[3,2-c]pyridine-2-sulfonamide

HRID 1383002Notes

Reaction equation

HRID 1383002 reaction equation
[CH3:1][C:2]1[C:3]2[O:10][CH:9]=[CH:8][C:4]=2[CH:5]=[N:6][CH:7]=1.C([N-:14]C(C)C)(C)C.[Li+].O.O.O.C([O-])(=O)C.[Na+].N[O:28][S:29]([OH:32])(=O)=O>O1CCCC1.CCCCCC>[S:29]([C:9]1[O:10][C:3]2[C:2]([CH3:1])=[CH:7][N:6]=[CH:5][C:4]=2[CH:8]=1)(=[O:32])(=[O:28])[NH2:14]

Participants

7

Reactant 4

HCID 76284hydroxylamine-O-sulfonic acidHCID 2724682Lithium diisopropylamideHCID 14372149HCID 14372149, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 143721337-Methylfuro[3,2-c]pyridine-2-sulfonamideYield 58%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 7-methylfuro[3,2-c]pyridine (1.33 g, 10 mmol) in distilled tetrahydrofuran (20 ml), under a nitrogen atmosphere and cooled to -70° C., was added dropwise 0.7M lithium diisopropylamide in tetrahydrofuran (15.5 ml, 11 mmol) to give a gummy precipitate. After stirring for 0.5 hour, sulfur dioxide gas was bubbled over the reaction surface to give a white precipitate. After slowly warming this mixture to room temperature, hexane was added and the precipitate collected by filtration. This precipitate was washed with diethyl ether and air dried. The resultant lithium sulfinate salt (3.5 g) was dissolved in water (25 ml) and sodium acetate trihydrate (8.2 g, 60 mmol) and hydroxylamine-O-sulfonic acid (2.33 g, 20 mmol) were added. After stirring for 20 hours, the precipitated product was collected by filtration, then dissolved in ethyl acetate/methanol, dried over anhydrous sodium sulfate and filtered through a charcoal pad. The resultant solution was evaporated and the residue triturated with diethyl ether to give solid product (1.24 g, 58% yield). Recrystallization from ethyl acetate gave 1.1 g, m.p. 179.5°-181.5° C.

Workup

  1. customto give a gummy precipitate
  2. customsulfur dioxide gas was bubbled over the reaction surface
  3. customto give a white precipitate
  4. filtrationthe precipitate collected by filtration
  5. washThis precipitate was washed with diethyl ether and air
  6. customdried
  7. dissolutionThe resultant lithium sulfinate salt (3.5 g) was dissolved in water (25 ml)
  8. stirringAfter stirring for 20 hours
  9. filtrationthe precipitated product was collected by filtration
  10. dissolutiondissolved in ethyl acetate/methanol
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered through a charcoal pad
  13. customThe resultant solution was evaporated
  14. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-58f7722be759490393017ab02ba1e57c
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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