Sodium Bicarbonate → 3-{3-[(E)-2-Phenylethenesulfonylamino]phenyl}acrylic acid methyl ester

HRID 226159Notes

Reaction equation

HRID 226159 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15](=[O:25])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.O>[CH3:13][O:14][C:15](=[O:25])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][S:9](/[CH:8]=[CH:7]/[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:11])=[O:10])[CH:19]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5369377(E)-2-phenylethene-1-sulfonyl chlorideHCID 54385173Methyl 3-aminocinnamate

Product 1

HCID 670195993-{3-[(E)-2-Phenylethenesulfonylamino]phenyl}acrylic acid methyl esterYield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of (E)-2-phenylethenesulfonyl chloride (24a) (0.59 g, 2.82 mmol) in dioxane (3 ml) was added to a mixture of 3-(3-aminophenyl)-acrylic acid methyl ester (23) (0.50 g, 2.82 mmol) in dioxane (12 ml) and NaHCO3 (0.36 g, 4.28 mmol) in water (8 ml), and the resultant solution was stirred at room temperature until the completion of the reaction (control by TLC). The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with chloroform-ethyl acetate (100:2, v/v) as eluent to give the title compound (0.68 g, 70%) as a white solid. 1H NMR (CDCl3, HMDSO), δ: 3.78 (3H, s); 6.39 (1H, d, J=16.0 Hz); 6.77 (1H, d, J=15.8 Hz); 6.78 (1H, s); 7.17-7.48 (9H, m); 7.49 (1H, d, J=15.8 Hz); 7.58 (1H, d, J=16.0 Hz).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel with chloroform-ethyl acetate (100:2

Sources & evidence

ORD record
ord-794ff716d7644b8a9501b4c7092df5f9
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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