Hydrochloric Acid → HCID 58521933, compound

HRID 2390258Notes

Reaction equation

HRID 2390258 reaction equation
[Br:1][C:2]1[C:3]([CH:14](C(OCC)=O)C(OCC)=O)=[N:4][CH:5]=[C:6]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:7]=1.Cl>O>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([N:11]([CH3:12])[CH3:13])(=[O:10])=[O:9])[CH:5]=[N:4][C:3]=1[CH3:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67008743HCID 67008743, compound

Product 1

HCID 58521933HCID 58521933, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethyl {3-bromo-5-[(dimethylamino)sulfonyl]pyridin-2-yl}malonate (222 mg; 0.52 mmol) was treated with a 5 N solution of HCl in water (11 ml) and the resulting solution was refluxed for 6 h. The solvent was removed under reduced pressure, and the solid residue was carefully quenched with a saturated Na2CO3 solution in water. The resulting suspension was extracted with AcOEt. The organic phase was washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to give the title compound as a white solid (125 mg; 86% yield).

Workup

  1. temperaturethe resulting solution was refluxed for 6 h
  2. customThe solvent was removed under reduced pressure
  3. customthe solid residue was carefully quenched with a saturated Na2CO3 solution in water
  4. extractionThe resulting suspension was extracted with AcOEt
  5. washThe organic phase was washed with brine
  6. customdried on MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5deaca31b3bb49a4a312272f7284f773
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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