4-(3-(N-methylsulfamoyl)phenyloxy)benzene → 4-(3-(N-methylsulfamoyl)phenyloxy)-1-nitrobenzene

HRID 1768294Notes

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

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 5 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. Step 4. Synthesis of 4-(3-(N-methylsulfamoyl)phenyloxy)aniline

Workup

temperatureto warm to room 5 temp
concentration, and was 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-f864796e59b041dba6a408f347ea2eef
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235576B1

Reaction notes

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