Potassium Carbonate → 2-(3-Methoxyphenyl)-4-(4-nitrophenyl)sulfonyl-morpholine

HRID 880238Notes

Reaction equation

HRID 880238 reaction equation
Br[CH2:2][CH:3]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)[O:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)(=[O:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CCOC(C)=O>[CH3:27][O:26][C:22]1[CH:21]=[C:20]([CH:3]2[O:4][CH2:5][CH2:6][N:7]([S:8]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)(=[O:10])=[O:9])[CH2:2]2)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 89725923N-[2-[2-Bromo-1-(3-methoxyphenyl)ethoxy]ethyl]-4-nitro-benzenesulfonamide

Product 1

HCID 897259362-(3-Methoxyphenyl)-4-(4-nitrophenyl)sulfonyl-morpholineYield 95.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve N-[2-[2-bromo-1-(3-methoxyphenyl)ethoxy]ethyl]-4-nitro-benzenesulfonamide (14.22 g, 30.96 moles) in ACN (200 mL); add potassium carbonate (6.42 g, 46.44 mmol); and heat the mixture to reflux. Stir the mixture for 3 h while refluxing. Cool the resulting mixture to ambient temperature and dilute it with EtOAc. Filter through Celite®; concentrate the filtrate under reduced pressure to provide a residue. Purify the residue via flash column chromatography eluting with a 50-80% gradient of EtOAc in hexanes. Combine the product fractions and remove the solvents under reduced pressure to provide the title compound as an orange solid (11.2 g, 95.6%). MS (m/z): 379 (M+1).

Workup

  1. temperatureand heat the mixture
  2. temperatureto reflux
  3. temperaturewhile refluxing
  4. filtrationFilter through Celite®
  5. concentrationconcentrate the filtrate under reduced pressure
  6. customto provide a residue
  7. customPurify the residue via flash column chromatography
  8. washeluting with a 50-80% gradient of EtOAc in hexanes
  9. customCombine the product fractions and remove the solvents under reduced pressure

Sources & evidence

ORD record
ord-d8a982c28dd04554beb21e55cd89639f
Source dataset
uspto-grants-2015_03
Patent number
US08993568B2

Reaction notes

Loading…