Pyridine → Methyl 3-[3-(phenylsulfamoyl)phenyl]prop-2-enoate

HRID 351029Notes

Reaction equation

HRID 351029 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:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CC=CC=1>ClCCl>[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:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 737087423-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

Product 1

HCID 67019508Methyl 3-[3-(phenylsulfamoyl)phenyl]prop-2-enoateYield 29.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(3-chlorosulfonylphenyl)acrylic acid methyl ester (3) (0.640 g, 2.45 mmol) in dichloromethane (2 ml) was added to a mixture of aniline (0.465 g, 4.99 mmol) and pyridine (1 ml), and the resultant solution was stirred at 50° C. for one hour. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 10% 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 (7:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.226 g, 29%). 1H NMR (CDCl3, HMDSO), δ: 3.72 (3H, s); 6.34 (1H, d, J=16.0 Hz); 6.68 (1H, br s); 6.92–7.89 (10H, m).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 10% 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 (7:1
  7. washThe obtained product was washed with diethyl ether

Sources & evidence

ORD record
ord-91c50d2d954840e7ad4950e73da56166
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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