Pyridine → HCID 67019559, compound

HRID 351075Notes

Reaction equation

HRID 351075 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>ClCCl>[C:2]1([NH:1][S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 38309693-(4-Chlorosulfonyl-phenyl)-acrylic acid

Product 1

HCID 67019559HCID 67019559, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of aniline (0.35 g, 3.75 mmol) and pyridine (1 ml) a solution of 3-(4-chlorosulfonyl-phenyl)acrylic acid (42) (0.45 g, 1.82 mmol) in dichloromethane (3 ml) was added and the resultant solution was stirred at 40° C. for 1 hour. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 6N HCl. The organic layer was washed successively with water, saturated NaCl and dried (Na2SO4). The solvent was evaporated under reduced pressure to give the title compound (0.30 g, 54%). 1H NMR (DMSO-d6, HMDSO), δ: 6.60 (1H, d, J=16.0 Hz); 6.93–7.43 (5H, m); 7.60 (1H, d, J=16.0 Hz); 7.79 (2H, d, J=8.0 Hz); 7.87 (2H, d, J=8.0 Hz); 10.35 (1H, s).

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated
  3. customthe residue was partitioned between ethyl acetate and 6N HCl
  4. washThe organic layer was washed successively with water, saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-dc320e661eb14102923742d367a4071a
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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