Benzenesulfonyl chloride → N-{5-[2-(4-Cyanophenyl)ethoxy]-2-methylphenyl}benzenesulfonamide

HRID 1791858Notes

Reaction equation

HRID 1791858 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH:15]=[CH:14][C:13]=1[CH3:29].C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][O:18][C:16]2[CH:15]=[CH:14][C:13]([CH3:29])=[C:12]([NH:11][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:17]=2)=[CH:22][CH:23]=1)#[N:28]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22033532Amino-5-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

Product 1

HCID 22033468N-{5-[2-(4-Cyanophenyl)ethoxy]-2-methylphenyl}benzenesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (22 μL; 0.17 mmol) was added to a cold solution (ice:water temperature) of amino-5-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene (0.041 g; 0.16 mmol; from step (ii) above) in pyridine (4 mL) The reaction flask was left overnight in a refrigerator. NaHCO3/aq (sat.) was added and the solution extracted twice with EtOAc. The combined organic phases were washed with water, HCl/aq (2M) and water. Drying (MgSO4) and evaporation of the solvent in vacuo afforded 0.062 g (100%) of the sub-title compound.

Workup

  1. extractionthe solution extracted twice with EtOAc
  2. washThe combined organic phases were washed with water, HCl/aq (2M) and water
  3. customDrying
  4. custom(MgSO4) and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-b6cc1b52f1bd4a2782218856645c0bae
Source dataset
uspto-grants-2006_07
Patent number
US07074820B2

Reaction notes

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