Hydrochloric Acid → 2-Bromo-N-ethylbenzene-1-sulfonamide

HRID 1523746Notes

Reaction equation

HRID 1523746 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[CH2:12]([NH2:14])[CH3:13].Cl.CCOC(C)=O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:14][CH2:12][CH3:13])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 8857Ethyl AcetateHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 163848002-Bromo-N-ethylbenzene-1-sulfonamideYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 20 mL vial were added a stirbar, 2-bromobenzene-1-sulfonyl chloride (0.995 g, 3.89 mmol), and THF (5 mL). The vial was then charged with EtNH2 in THF (5 mL, 2.0 M). The mixture was stirred for 24 hours before adding it to a separatory funnel containing 1 N HCl and EtOAc. The layers were mixed thoroughly and then separated. The organic layer was then washed with water followed by sat. NaHCO3, dried over MgSO4, filtered and concentrated to dryness to give the crude product. Subjecting the oil to FCC yielded the title compound (580 mg, 56%). 1H NMR (600 MHz, CDCl3) δ 8.17-8.10 (dd, J=7.8, 1.7, 1H), 7.75-7.69 (dd, J=7.8, 1.2, 1H), 7.48-7.43 (m, 1H), 7.43-7.37 (m, 1H), 5.16-4.91 (t, J=6.7, 1H), 3.06-2.87 (m, 2H), 1.19-1.00 (t, J=7.3, 3H).

Workup

  1. additionbefore adding it to a separatory funnel
  2. additionThe layers were mixed thoroughly
  3. customseparated
  4. washThe organic layer was then washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customto give the crude product

Sources & evidence

ORD record
ord-7506b553a29242bfaf4306f2c61aecee
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…