p-Bromobenzenesulfonyl chloride → HCID 1377400, compound

HRID 731584Notes

Reaction equation

HRID 731584 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[NH2:22])[CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:22][C:20]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:21]=2[N:12]=[CH:13][CH:14]=[CH:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 113598-Aminoquinoline

Product 1

HCID 1377400HCID 1377400, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-bromobenzene sulfonylchloride (1.10 g, 4.32 mmol) in pyridine (5 mL) was added 8-quinolinamine (1, 623 mg, 4.32 mmol) and the reaction mixture was stirred overnight at 25° C. Ethyl acetate was added to the reaction mixture and the organic layer was washed with saturated sodium carbonate (X 3), dried over magnesium sulfate, filtered and concentration under reduced pressure to afford a light brown solid (2, 1.57 g, 3.80 mmol). MS(ESI) [M+H+]+=363.1; 365.1 (1:1)

Workup

  1. washthe organic layer was washed with saturated sodium carbonate (X 3)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentration under reduced pressure
  5. customto afford a light brown solid (2, 1.57 g, 3.80 mmol)

Sources & evidence

ORD record
ord-430b398584c648fd9afb9b279110da20
Source dataset
uspto-grants-2009_09
Patent number
US07585859B2

Reaction notes

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