2-Naphthylamine → 3-[3-(Naphthalen-2-ylsulfamoyl)-phenyl]-acrylic acid methyl ester

HRID 2180410Notes

Reaction equation

HRID 2180410 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[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[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[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 70572-NaphthylamineHCID 516892Sodium BicarbonateHCID 737087423-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

Product 1

HCID 670194963-[3-(Naphthalen-2-ylsulfamoyl)-phenyl]-acrylic acid methyl esterYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(3-chlorosulfonylphenyl)acrylic acid methyl ester (3) (1.0 g, 3.83 mmol) in dioxane (10 ml) was added to a mixture of 2-aminonaphthalene (0.55 g, 3.83 mmol) and NaHCO3 (0.48 g, 5.71 mmol) in water (6 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 (3:2, v/v) as eluent. The obtained product was crystallised from petroleum ether-ethyl acetate to give the title compound (0.52 g, 34%) as a white solid. 1H NMR (DMSO-d6, HMDSO), δ: 3.73 (3H, s); 6.67 (1H, d, J=16.0 Hz); 7.21-8.07 (11H, m); 8.16 (1H, s); 10.55 (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 (3:2
  7. customThe obtained product was crystallised from petroleum ether-ethyl acetate

Sources & evidence

ORD record
ord-d99fc6cac0cf4e40ac696b62412b88c2
Source dataset
uspto-grants-2005_05
Patent number
US06888027B2

Reaction notes

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