Dimethylamine → HCID 4730021, compound

HRID 2390256Notes

Reaction equation

HRID 2390256 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8].[CH2:13]([N:15](CC)[CH2:16]C)C.CNC.CCO>C(Cl)Cl.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([N:15]([CH3:16])[CH3:13])(=[O:11])=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 702EthanolHCID 8471TriethylamineHCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chloride

Product 1

HCID 4730021HCID 4730021, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of 5-bromo-6-chloropyridine-3-sulfonyl chloride (2.00 g; 6.87 mmol) in DCM (20 mL) was treated first with triethylamine (1.06 ml; 7.56 mmol) then with a 5.6 M solution of dimethylamine in EtOH (1.35 ml; 7.56 mmol). The reaction was stirred at 0° C. for 1.5 hours then brine was added and the phases separated. The organic phase was washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to give a residue which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound as a colorless oil.

Workup

  1. customthe phases separated
  2. washThe organic phase was washed with brine
  3. customdried on MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue which
  7. customwas purified by flash column chromatography (silica)
  8. washeluting with cyclohexane containing
  9. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-092d46865088455f9af5f748f3df91c6
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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