Potassium Carbonate → HCID 23521674, compound

HRID 392450Notes

Reaction equation

HRID 392450 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[CH3:9])=[CH:4][CH:3]=1.Cl.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23]Cl)[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([N:10]([CH2:23][C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)[S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[CH3:9])=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochloride2×HCID 3817108HCID 3817108, compound

Product 1

HCID 23521674HCID 23521674, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(1-(4-Bromophenyl)ethyl)-N-ethylsulfonylamine (1.25 g, 4.28 mmol), and (0.75 g, 4.6 mmol) of 3-picolyl chloride hydrochloride, and (5.1 g, 37 mmol) of potassium carbonate were dissolved in 40 ml DMF. Additional 3-picolyl chloride hydrochloride (0.75 g, 4.6 mmol) was added after 30 minutes and the mixture stirred 20 h at room temperature. The mixture was diluted with 120 ml ethyl acetate and 60 ml of water and transferred to a separatory funnel. The organic layer was separated and washed twice with water. The organic layer was again separated and dried over sodium sulfate, filtered, and concentrated in vacuo to afford a dark oil. The oil was purified by radial chromatography on a 6 micron silica plate eluting with 1 to 4% methanol/dichloromethane to afford after concentration of fractions the title compound. MS calcd. 383.2; MS (M+1) 384.1.

Workup

  1. customtransferred to a separatory funnel
  2. customThe organic layer was separated
  3. washwashed twice with water
  4. customThe organic layer was again separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a dark oil
  9. customThe oil was purified by radial chromatography on a 6 micron silica plate
  10. washeluting with 1 to 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-8a82a4a0f7b64841b07ccbd0c395f5c7
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

Loading…