Sulfur Dioxide → HCID 19434080, compound

HRID 1736024Notes

Reaction equation

HRID 1736024 reaction equation
[CH3:1][CH:2]([N:4]1[C:9]([CH2:10][OH:11])=[CH:8][C:7]2[CH:12]=[CH:13][S:14][C:6]=2[S:5]1(=[O:16])=[O:15])[CH3:3].C([Li])CCC.[S:22](=[O:24])=[O:23].[NH2:25]OS(O)(=O)=O.CC([O-])=O.[Na+]>C1COCC1.O>[OH:11][CH2:10][C:9]1[N:4]([CH:2]([CH3:1])[CH3:3])[S:5](=[O:16])(=[O:15])[C:6]2[S:14][C:13]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:12][C:7]=2[CH:8]=1

Participants

8

Reactant 5

HCID 1119Sulfur DioxideHCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 19434117HCID 19434117, compoundHCID 178418339Butyllithium

Product 1

HCID 19434080HCID 19434080, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step D (3.25 g, 12.5 mmol) in anhydrous THF (60 mL) under nitrogen at -70° C. was added n-butyllithium (2.5M, 12.5 mL, 31.4 mmol) over 5 min. The suspension was stirred for 1 h before a stream of sulfur dioxide was passed over the surface of the reaction mixture for 5 min. The mixture was warmed to ambient temperature and evaporated to give a residue which was combined with water (100 mL); this mixture was cooled (ice bath) and hydroxylamine-O-sulfonic acid (4.24 g, 37.5 mmol) and NaOAc (8.5 g, 62.5 mmol) were added. The reaction mixture was stirred at ambient temperature for 18 h and extracted with ethyl acetate (2×200 mL). The combined extracts were dried (MgSO4), filtered, and evaporated to a residue which was purified by column chromatography (silica, 50% ethyl acetate/hexane) to give a viscous oil (4.20 g, 98%).

Workup

  1. customevaporated
  2. customto give a residue which
  3. additionwere added
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to a residue which
  8. customwas purified by column chromatography (silica, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c73ff1ab6b0648b48c88d577eec09db9
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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