Water → HCID 58237114, compound

HRID 1188945Notes

Reaction equation

HRID 1188945 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 15%

Conditions

Temperature
90 °C

Procedure

A mixture of p-toluenesulfonic acid hydrate (1.03 g) and toluene (15 mL) was refluxed for 2 h with azeotropic removal of water, and then cooled to 90° C. A solution of ethyl 2-[(2-methoxy-4-{[6-(methoxymethyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoate (1.0 g) in toluene (10 mL) was added to the mixture at 90° C. The whole was stirred at 90° C. for 1 h, and then refluxed for 2 h. An aqueous solution of sodium hydrogen carbonate was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:4 to 2:1, volume ratio) and then by silica gel chromatography (ethyl acetate:hexane=1:9 to 2:1, volume ratio) to give the title compound (140 mg, 15%) as pale yellow crystals. MS 357 (MH+).

Workup

  1. temperaturerefluxed for 2 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:4 to 2:1, volume ratio)

Sources & evidence

ORD record
ord-eb1b89574f9f4bb7a09b7876a441ac09
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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