Pyridine → HCID 67019617, compound

HRID 226164Notes

Reaction equation

HRID 226164 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:14][O:15][C:16](=[O:29])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:14][O:15][C:16](=[O:29])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](=[O:26])(=[O:27])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6115AnilineHCID 73708739HCID 73708739, compound

Product 1

HCID 67019617HCID 67019617, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of aniline (0.33 g, 3.53 mmol) and pyridine (1 ml) a solution of 3-(2-chlorosulfonylphenyl)acrylic acid methyl ester (33) (0.45 g, 1.72 mmol) in dichloromethane (3 ml) was added and the resultant solution was stirred at 50° C. for 1 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 ethyl acetate-chloroform (1:7, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.33 g, 60%). 1H NMR (CDCl3, HMDSO), δ: 3.86 (3H, s); 6.27 (1H, d, J=16.0 Hz); 6.69 (1H, br s); 6.87-7.67 (8H, m); 7.94-8.13 (1H, m); 8.49 (1H, d, J=16.0 Hz).

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated
  3. customthe residue was partitioned between ethyl acetate and 10% HCl
  4. washThe organic layer was washed successively with water, saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed
  7. customthe residue was chromatographed on silica gel with ethyl acetate-chloroform (1:7
  8. washThe obtained product was washed with diethyl ether

Sources & evidence

ORD record
ord-2843d76c46d249168e828bdb643790d2
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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