Ammonia → 5-Chloronaphthalene-2-sulfonamide

HRID 528792Notes

Reaction equation

HRID 528792 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12](Cl)(=[O:14])=[O:13])=[CH:7]2.[NH3:16]>>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([NH2:16])(=[O:14])=[O:13])=[CH:7]2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 27357775-Chloronaphthalene-2-sulphonyl chloride

Product 1

HCID 197086955-Chloronaphthalene-2-sulfonamideYield 40.8%

Procedure

5-Chloronaphthalene-2-sulfonyl chloride (Toronto, 531 mg, 2.03 mmol) was treated with NH3 (10.2 mL, 5.08 mmol, 0.5M solution in dioxanes) and stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo, redissolved in sat. aq. NaHCO3 solution and extracted with CHCl3 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (200 mg, 37%). 1H NMR (DMSO-d6) δ 8.53 (d, J=1.8 Hz, 1H), 8.36 (d, J=9.0 Hz, 1H), 8.18 (d, J=8.6 Hz, 1H), 8.06 (d, J=9.0 Hz, 1H), 7.87 (d, J=7.5 Hz, 1H), 7.70-7.62 (m, 1H); MS(ESI−) m/z 240.3 (M−H)−.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionredissolved in sat. aq. NaHCO3 solution
  3. extractionextracted with CHCl3 (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd48fb9408144db4b07581ef1b82270c
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

Loading…