4-(3-(N-methylsulfamoyl)phenyloxy)benzene → 4-(3-(N-methylsulfamoyl)phenyloxy)-1-nitrobenzene
Reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].[N:19]([O-:21])=[O:20].[Na+]>C(O)(C(F)(F)F)=O>[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a solution of 4-(3-(N-methylsulfamoyl)phenyloxy)benzene (0.30 g, 1.14 mmol) in TFA (6 mL) at −10° C. was added NaNO2 (0.097 g, 1.14 mmol) in portions over 5 min. The resulting solution was stirred at −10° C. for 1 h, then was allowed to warm to room temp., and was concentrated under reduced pressure. The residue was separated between EtOAc (10 mL) and water (10 mL). The organic phase was sequentially washed with water (10 mL) and a saturated NaCl solution (10 mL), dried (MgSO4) and concentrated under reduced pressure to give 4-(3-(N-methylsulfamoyl)phenyloxy)-1-nitrobenzene (0.20 g). This material carried on to the next step without further purification.
Workup
- temperatureto warm to room temp.
- concentrationwas concentrated under reduced pressure
- customThe residue was separated between EtOAc (10 mL) and water (10 mL)
- washThe organic phase was sequentially washed with water (10 mL)
- dry with materiala saturated NaCl solution (10 mL), dried (MgSO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3ec0b26341244a3bb8e567383187831a
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351834B1
Reaction notes
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