Benzenesulfonyl chloride → N-(3-iodophenyl)benzenesulfonamide

HRID 2402409Notes

Reaction equation

HRID 2402409 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CCN(CC)CC.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:16]1([S:22]([NH:5][C:4]2[CH:3]=[C:2]([I:1])[CH:8]=[CH:7][CH:6]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 122713-IodoanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 1009990N-(3-iodophenyl)benzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-iodoaniline (5 g, 22.8 mmol), in CH2Cl2 (100 mL), were added at room temperature Et3N (6.97 mL) followed by benzenesulfonyl chloride (5.84 mL). The mixture was stirred 4 h then a white precipitate was formed. A saturated aqueous solution of NaHCO3 was added and the phases were separated. The aqueous layer was extracted several times with CH2Cl2 and the combined extracts were dried over (MgSO4) then evaporated. The crude mixture was dissolved in MeOH (100 mL) and NaOMe (6 g), was added and the mixture was heated 1 h at 60° C. The solution became clear with time and HCl (1N) was added. The solvent was evaporated under reduced pressure then the aqueous phase was extracted several times with CH2Cl2. The combined organic extracts were dried over (MgSO4) and evaporated. The crude material was purified by flash chromatography using (100% CH2Cl2) as solvent yielding the title compound 21 (7.68 g, 94%) as yellow solid.

Workup

  1. customa white precipitate was formed
  2. customthe phases were separated
  3. extractionThe aqueous layer was extracted several times with CH2Cl2
  4. dry with materialthe combined extracts were dried over (MgSO4)
  5. customthen evaporated
  6. dissolutionThe crude mixture was dissolved in MeOH (100 mL)
  7. additionNaOMe (6 g), was added
  8. additionwas added
  9. customThe solvent was evaporated under reduced pressure
  10. extractionthe aqueous phase was extracted several times with CH2Cl2
  11. dry with materialThe combined organic extracts were dried over (MgSO4)
  12. customevaporated
  13. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-fc0d3ec69bd64894916ec4e12caf2484
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

Loading…