2-Nitrobenzenesulfonyl chloride → Ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

HRID 507918Notes

Reaction equation

HRID 507918 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([F:15])[CH:3]=1.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17]>N1C=CC=CC=1>[F:15][C:4]1[CH:3]=[C:2]([NH:1][S:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N+:16]([O-:18])=[O:17])(=[O:26])=[O:27])[CH:7]=[CH:6][C:5]=1[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 23157234Ethyl 3-(4-amino-2-fluorophenyl)propanoate

Product 1

HCID 23157368Ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoateYield 76.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 3-(4-amino-2-fluorophenyl)propanoate (9.89 g, 46.8 mmol) in pyridine (70 mL) was added 2-nitrobenzenesulfonyl chloride (11.4 g, 51.5 mmol) by small portions, and the mixture was stirred at room temperature for 70 hr. The solvent was evaporated under reduced pressure, and water and ethyl acetate were added to the obtained residue. The mixture was stirred with heating at 80° C. for 15 min and filtrated through celite. The organic layer in the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-50% ethyl acetate/hexane) to give the title compound (14.2 g, yield 76%) as pale-yellow prism crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and ethyl acetate
  2. additionwere added to the obtained residue
  3. stirringThe mixture was stirred
  4. temperaturewith heating at 80° C. for 15 min
  5. filtrationfiltrated through celite
  6. washThe organic layer in the filtrate was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (20%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3b5f850073af42d18e1fe5ecd231c724
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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