Pyridine → N-{3-[2-(4-Cyanophenyl)ethoxy]phenyl}-2-chlorobenzenesulfonamide

HRID 325029Notes

Reaction equation

HRID 325029 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[CH:9]=1.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[C:23]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][O:14][C:10]2[CH:9]=[C:8]([NH:7][S:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[Cl:25])(=[O:34])=[O:33])[CH:13]=[CH:12][CH:11]=2)=[CH:22][CH:21]=1)#[N:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 22033543HCID 22033543, compound

Product 1

HCID 10873356N-{3-[2-(4-Cyanophenyl)ethoxy]phenyl}-2-chlorobenzenesulfonamideYield 36.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.255 mL; 3.15 mmol) was added to a stirred solution of amino-3-[2-(4-cyanophenyl)ethoxy]benzene (0.15 g; 0.629 mmol; from step (ii) above) and 2-chlorobenzenesulfonyl chloride (0.173 mL; 0.818 mmol) in CH2Cl2 (4 mL). After 45 minutes at room temperature the solvent was removed in vacuo. To remove traces of pyridine, EtOH was added and evaporated. The residue was partitioned between water and EtOAc. The organic layer was washed with 0.1M aqueous HCl and brine, dried (Na2SO4) and the solvent removed in vacuo. Purification by flash chromatography (SiO2; toluene:EtOAc (1:0 to 9:1)) afforded 0.095 g (35%) of the sub-title compound.

Workup

  1. customAfter 45 minutes at room temperature the solvent was removed in vacuo
  2. customTo remove traces of pyridine, EtOH
  3. additionwas added
  4. customevaporated
  5. customThe residue was partitioned between water and EtOAc
  6. washThe organic layer was washed with 0.1M aqueous HCl and brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed in vacuo
  9. customPurification by flash chromatography (SiO2; toluene:EtOAc (1:0 to 9:1))

Sources & evidence

ORD record
ord-b9229219405c4f0388bd3991ce3d5146
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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