Ethylene Oxide → N-[2-[2-Bromo-1-(3-methoxyphenyl)ethoxy]ethyl]-4-nitro-benzenesulfonamide

HRID 880237Notes

Reaction equation

HRID 880237 reaction equation
[CH2:1]1[O:3][CH2:2]1.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=[CH2:13])[CH:7]=1.[Br:14]N1C(=O)CCC1=O.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1)([O-:24])=[O:23]>C(Cl)Cl>[Br:14][CH2:13][CH:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH3:4])[CH:7]=1)[O:3][CH2:1][CH2:2][NH:34][S:31]([C:28]1[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=1)(=[O:32])=[O:33]

Participants

6

Reactant 4

HCID 6354Ethylene OxideHCID 227844-NitrobenzenesulfonamideHCID 67184N-bromobutanimideHCID 5841461-Ethenyl-3-methoxybenzene

Product 1

HCID 89725923N-[2-[2-Bromo-1-(3-methoxyphenyl)ethoxy]ethyl]-4-nitro-benzenesulfonamideYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add ethylene oxide (11 mL, 220 mmol) all at once to DCM cooled to 0° C.; then add 1-methoxy-3-vinylbenzene (7.09 g, 52.82 mmol) via a syringe. Stir the mixture while maintaining it 0° C. Add N-bromosuccinimide (9.4 g, 52.82 mmol) and 4-nitrobenzenesulfonamide (8.9 g, 44.02 mmol). Wrap flask in foil and stir the reaction mixture for 20 h while maintaining it at ambient temperature. Concentrate under reduced pressure; filter; and concentrate the filtrate under reduced pressure to provide a residue. Purify the residue via flash column chromatography eluting with a 5-40% gradient of EtOAc in hexanes. Combine the product fractions, and remove the solvents under reduced pressure to provide the title compound as a dark yellow oil (14.22 g, 70.3%). MS (m/z): 459 (M+1).

Workup

  1. temperaturewhile maintaining it 0° C
  2. stirringWrap flask in foil and stir the reaction mixture for 20 h
  3. temperaturewhile maintaining it at ambient temperature
  4. concentrationConcentrate under reduced pressure
  5. filtrationfilter
  6. concentrationand concentrate the filtrate under reduced pressure
  7. customto provide a residue
  8. customPurify the residue via flash column chromatography
  9. washeluting with a 5-40% gradient of EtOAc in hexanes
  10. customCombine the product fractions, and remove the solvents under reduced pressure

Sources & evidence

ORD record
ord-19be1b9dcfd144e2a36d63f8dc0900ad
Source dataset
uspto-grants-2015_03
Patent number
US08993568B2

Reaction notes

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