1-Naphthylamine → 3-[3-(Naphthalen-1-ylsulfamoyl)-phenyl]-acrylic acid methyl ester

HRID 351057Notes

Reaction equation

HRID 351057 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:7]=1.[NH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.O>[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](=[O:14])(=[O:13])[NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 86401-NaphthylamineHCID 516892Sodium BicarbonateHCID 737087423-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

Product 1

HCID 670195833-[3-(Naphthalen-1-ylsulfamoyl)-phenyl]-acrylic acid methyl esterYield 51.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-(3-chlorosulfonylphenyl)acrylic acid methyl ester (3) (0.4 g, 1.53 mmol) in dioxane (5 ml) was added to a mixture of 1-aminonaphthalene (0.22 g, 1.53 mmol) in dioxane (1 ml) and NaHCO3 (0.26 g, 3.09 mmol) in water (3 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 petroleum ether-ethyl acetate (gradient from 2:1 to 1:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.29 g, 51%) as a white solid. 1H NMR (DMSO-d6, HMDSO), δ: 3.69 (3H, s); 6.56 (1H, d, J=16.0 Hz); 7.16 (1H, dd, J=7.0 and 1.4 Hz); 7.27–8.14 (11H, m); 10.25 (1H, s).

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 petroleum ether-ethyl acetate (gradient from 2:1 to 1:1
  7. washThe obtained product was washed with diethyl ether

Sources & evidence

ORD record
ord-cbe7ce0e2f8f494e87e72aa61a67b05b
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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