((2-Chloroethyl)sulphonyl)benzene → 2-(Benzenesulfonyl)ethan-1-amine

HRID 1785768Notes

Reaction equation

HRID 1785768 reaction equation
Cl[CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].C1(=O)[NH:17]C(=O)C2=CC=CC=C12.[K].C1OCCOCCOCCOCCOCCOC1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1.C(OCC)(=O)C>[C:7]1([S:4]([CH2:3][CH2:2][NH2:17])(=[O:6])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 13646((2-Chloroethyl)sulphonyl)benzeneHCID 2855718-Crown-6HCID 24194345Phthalimide potassium salt

Product 1

HCID 35454972-(Benzenesulfonyl)ethan-1-amine

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of ((2-chloroethyl)sulfonyl)benzene (1.02 g, 5.0 mmol), potassium phthalimide (1.02 g, 5.5 mmol), 18-crown-6 (50 mg), and tetrabutylammonium iodide (50 mg) in dioxane was heated to reflux, stirred for 24 hours, cooled to room temperature, diluted with ethyl acetate (100 mL), washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in ethanol (10 mL), treated with hydrazine hydrate (1 mL), heated to reflux, stirred for 2 hours, cooled to room temperature, filtered through diatomaceous earth (Celite®), and rinsed with ethyl acetate. The filtrate was treated with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in diethyl ether (5 mL), treated with 1M HCl in diethyl ether (10 mL), and filtered. The solid was washed with diethyl ether, suspended in ethyl acetate (80 mL), washed with 2M Na2CO3 and brine, dried (MgSO4), filtered, and concentrated to provide the desired product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in ethanol (10 mL)
  8. additiontreated with hydrazine hydrate (1 mL)
  9. temperatureheated
  10. temperatureto reflux
  11. stirringstirred for 2 hours
  12. temperaturecooled to room temperature
  13. filtrationfiltered through diatomaceous earth (Celite®)
  14. washrinsed with ethyl acetate
  15. additionThe filtrate was treated with ethyl acetate
  16. washwashed with water and brine
  17. dry with materialdried (MgSO4)
  18. filtrationfiltered
  19. concentrationconcentrated
  20. dissolutionThe concentrate was dissolved in diethyl ether (5 mL)
  21. additiontreated with 1M HCl in diethyl ether (10 mL)
  22. filtrationfiltered
  23. washThe solid was washed with diethyl ether
  24. washwashed with 2M Na2CO3 and brine
  25. dry with materialdried (MgSO4)
  26. filtrationfiltered
  27. concentrationconcentrated

Sources & evidence

ORD record
ord-35c25e60eaeb49c7a1370fc539bea86a
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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