Hydrochloric Acid → HCID 20355557, compound

HRID 598531Notes

Reaction equation

HRID 598531 reaction equation
CC1C=CC(S(O[CH:12]([CH2:22][CH2:23][S:24](=[O:27])(=[O:26])[NH2:25])[CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].O.Cl>CN(C=O)C>[CH2:15]([O:14][CH2:13][CH:12]1[CH2:22][CH2:23][S:24](=[O:27])(=[O:26])[NH:25]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 57752488HCID 57752488, compound

Product 1

HCID 20355557HCID 20355557, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sulfonamide 6 (109 g, 0.26 mol) was dissolved in DMF (800 mL) and stirred at ambient temperature. To this was added K2CO3 (63 g, 0.46 mol) in one portion and the resultant mixture heated at reflux (oil bath 160° C.) for 3 hours. After this time the heating was ceased and the reaction allowed to cool with stirring overnight. The completed reaction was poured into water (1 L) and acidified with aqueous HCl (1 M, ˜500 mL) to pH 2. The resultant brown suspension was extracted with DCM (5×500 mL) and the combined organics washed with brine (1 L). A thick emulsion formed which was separated by the addition of iPrOAc until two distinct layers were visible. The organics were separated, dried (MgSO4) and evaporated to give an orange oil (66 g). This oil was purified by flash column chromatography (silica gel, 5% MeOH/DCM) to yield dioxide 7 as a yellow-orange oil (40 g, 64%).

Workup

  1. temperatureat reflux (oil bath 160° C.) for 3 hours
  2. temperatureto cool
  3. stirringwith stirring overnight
  4. customThe completed reaction
  5. extractionThe resultant brown suspension was extracted with DCM (5×500 mL)
  6. washthe combined organics washed with brine (1 L)
  7. customA thick emulsion formed which
  8. customwas separated by the addition of iPrOAc until two distinct layers
  9. customThe organics were separated
  10. dry with materialdried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-73ec896cd193440982b759976423883d
Source dataset
uspto-grants-2011_03
Patent number
US07897629B2

Reaction notes

Loading…