Benzenesulfonyl chloride → HCID 22033525, compound

HRID 325034Notes

Reaction equation

HRID 325034 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]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[C:13]=1[CH3:29]>N1C=CC=CC=1>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][O:18][C:14]2[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]=[CH:16][CH:15]=2)=[CH:22][CH:23]=1)#[N:28]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 22033540Amino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

Product 1

HCID 22033525HCID 22033525, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (0.24 mL; 1.9 mmol) was added to a stirred solution of amino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene (0.42 g; 1.7 mmol; from step (iii) above) in dry pyridine (20 mL) under nitrogen. The reaction was left overnight at room temperature. After evaporation of the solvent the residue was partitioned between 10% aqueous HCl and EtOAc. The organic layer was washed with brine, dried (MgSO4) and the solvent removed in vacuo. Purification by flash chromatography afforded 0.47 g (72%) of the sub-title compound.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas partitioned between 10% aqueous HCl and EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-e0db434525a843a8b594c247d886eb75
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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