3-Pyridinecarboxaldehyde → 2-Trimethylsilyl-ethanesulfonic acid pyridin-3-ylmethyleneamide

HRID 1691831Notes

Reaction equation

HRID 1691831 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)=O.[CH3:9][Si:10]([CH3:18])([CH3:17])[CH2:11][CH2:12][S:13]([NH2:16])(=[O:15])=[O:14].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.B(F)(F)F.CCOCC>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH:1]=[N:16][S:13]([CH2:12][CH2:11][Si:10]([CH3:18])([CH3:17])[CH3:9])(=[O:15])=[O:14])[CH:4]=1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 110085532-(Trimethylsilyl)ethane-1-sulfonamide

Product 1

HCID 669074992-Trimethylsilyl-ethanesulfonic acid pyridin-3-ylmethyleneamideYield 102.2%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 3-formylpyridine (0.228 mL, 2.42 mmol) and 2-(trimethylsilyl)ethanesulfonamide (0.438 g, 2.42 mmol) in toluene (30 mL) was added boron trifluoride etherate (0.02 mL, 0.15 mmol) under Ar. The mixture was heated at reflux for 20 hours using a Dean-Stark trap. After cooling, 10% aqueous sodium bicarbonate was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to dryness to under reduced pressure obtain crude 2-trimethylsilyl-ethanesulfonic acid pyridin-3-ylmethyleneamide (669 mg), which was used directly in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness to under reduced pressure

Sources & evidence

ORD record
ord-0402079cafe649ab93fc21add1568145
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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