m-Bromobenzenesulphonyl chloride → HCID 57751032, compound

HRID 2283287Notes

Reaction equation

HRID 2283287 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([NH2:22])(=[O:21])=[O:20]>N1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([NH2:22])(=[O:20])=[O:21])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 17943m-Bromobenzenesulphonyl chlorideHCID 728942-Aminobenzenesulfonamide

Product 1

HCID 57751032HCID 57751032, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-benzenesulfonyl chloride (8.34 mL, 57.9 mmol) was added to a solution of 2-amino-benzenesulfonamide (9.965 g, 57.9 mmol) dissolved in pyridine (90 mL). The reaction was stirred for 4 h followed by solvent removal under vacuo. The reaction mixture was added to water and the product was extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated to furnish a dark yellow oil. The oil was dissolved in EtOAc and precipitated by addition of heptane. The solid was finally recrystallized from EtOH to give the title compound (10.784 g, 48%) as a white solid.

Workup

  1. customfollowed by solvent removal under vacuo
  2. additionThe reaction mixture was added to water
  3. extractionthe product was extracted three times with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto furnish a dark yellow oil
  9. customprecipitated by addition of heptane
  10. customThe solid was finally recrystallized from EtOH

Sources & evidence

ORD record
ord-41af0ff7580945f4af61d1bc4095ccac
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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