1-Naphthalenemethanamine → 3-{3-[(Naphthalen-1-ylmethyl)-sulfamoyl]-phenyl}-acrylic acid methyl ester

HRID 226137

Reaction equation

HRID 226137 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.[C:17]1([CH2:27][NH2:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=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:28][CH2:27][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 83551-NaphthalenemethanamineHCID 516892Sodium BicarbonateHCID 737087423-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

Product 1

HCID 670195403-{3-[(Naphthalen-1-ylmethyl)-sulfamoyl]-phenyl}-acrylic acid methyl esterYield 76%

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-naphthalenemethylamine (0.24 g, 1.53 mmol) in dioxane (1 ml) and NaHCO3 (0.25 g, 3.06 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 NaCl1 and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with petroleum ether-ethyl acetate (2:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.44 g, 76%) as a white solid. 1H NMR (DMSO-d6, HMDSO), δ: 3.74 (3H, s); 4.47 (2H, d, J=6.0 Hz); 6.69 (1H, d, J=16.0 Hz); 7.32-8.32 (13H, m).

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 NaCl1
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel with petroleum ether-ethyl acetate (2:1
  7. washThe obtained product was washed with diethyl ether

Sources & evidence

ORD record
ord-ce6780fef75c4923a829dacb12c62c8f
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Linked notes

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