Water → HCID 58237114, compound

HRID 1188931Notes

Reaction equation

HRID 1188931 reaction equation
O.[C:2]1(C)C=CC(S(O)(=O)=O)=C[CH:3]=1.O.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[CH:24]=[N:25][C:26]([CH2:29][O:30][CH3:31])=[CH:27][CH:28]=2)[CH:19]=[CH:18][C:17]=1[NH:32]N=C(C)C(OCC)=O.[C:41](=[O:44])([O-])[OH:42].[Na+].[C:46]1(C)C=CC=C[CH:47]=1>>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][C:23]2[CH:24]=[N:25][C:26]([CH2:29][O:30][CH3:31])=[CH:27][CH:28]=2)[CH:19]=[C:18]2[C:17]=1[NH:32][C:3]([C:41]([O:42][CH2:46][CH3:47])=[O:44])=[CH:2]2

Participants

6

Reactant 5

HCID 962WaterHCID 1140Toluene2×HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 76710730HCID 76710730, compound

Product 1

HCID 58237114HCID 58237114, compoundYield 21%

Conditions

Temperature
110 °C

Procedure

p-Toluenesulfonic acid monohydrate (11.8 g) was refluxed in toluene (200 mL) for 2 h with azeotropic removal of water. The mixture was cooled to 110° C. and a solution of ethyl 2-[(2-methoxy-4-{[6-(methoxymethyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoate (11.58 g) in toluene (50 mL) was added. The mixture was stirred at 110° C. for 5.5 h. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate solution was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90 to 75/25), followed by basic silica gel column chromatography (ethyl acetate/hexane=10/90 to 50/50, volume ratio) to afford a yellow solid. The solid was washed with diethyl ether to give the title compound (2.32 g, 21%) as a yellow solid. MS 357 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90 to 75/25)
  8. customto afford a yellow solid
  9. washThe solid was washed with diethyl ether

Sources & evidence

ORD record
ord-1c428b88e1bc4d84a0ce6f4f3d263c0d
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…