Ethanol → HCID 22506528, compound

HRID 985364Notes

Reaction equation

HRID 985364 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:10])[CH3:9].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18]>ClCCl>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([C:8](=[O:10])[CH3:9])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 3787675Pyridine-2-sulfonyl Chloride

Product 1

HCID 22506528HCID 22506528, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of triethylamine (0.86 g, 8.51 mmol, 2.2 equiv.) in dichloromethane (3 mL) at 0° C. was added ethanol (0.18 g, 3.87 mmol, 1 equiv.) followed by the addition of 2-pyridylsulfonyl chloride (0.83 g, 4.65 mmol, 1.2 equiv.). After stirring for 4 hours at 0° C., the solution was concentrated under reduced pressure. The concentrate was dissolved in aqueous NaHCO3 solution (50 mL) and extracted with diethyl ether (3×50 mL). The ether extracts were combined and washed with aqueous NaCl (50 mL), dried (MgSO4), and concentrated under reduced pressure. Column chromatography (5% EtOAc/Hex) afforded 16 (95%): 1H NMR (CDCl3, 400 MHz) δ 8.70 (d, J=4.7 Hz, 1H, ArH), 7.95 (p, J=6.4 Hz, 2H, ArH), 7.56 (t, J=5.3 Hz, 1H, ArH), 4.37 (q, J=7.0 Hz, 2H, CH2OSO2R), 1.29 (t, J=7.0 Hz, 3H); MALDI-FTMS 188.0000 (C6H9NOS+H30 requires 188.0376).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. dissolutionThe concentrate was dissolved in aqueous NaHCO3 solution (50 mL)
  3. extractionextracted with diethyl ether (3×50 mL)
  4. washwashed with aqueous NaCl (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e9a676bfbc0847be9318f82560dec14f
Source dataset
uspto-grants-2005_03
Patent number
US06872574B2

Reaction notes

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