N-(4-Chloro-2-nitrophenyl)benzenesulfonamide → 2-Phenylsulfonylamino-5-chloroaniline

HRID 1006535Notes

Reaction equation

[C:1]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[N+:18]([O-])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.C(OCC)(=O)C>[C:1]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[NH2:18])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-phenylsulfonylamino-5-chloro-1-nitrobenzene (172 mg; prepared in Reference Example 11.) in acetic acid (4 ml), reduced iron powder (154 mg) was added at room temperature under an atmosphere of argon. The suspension was stirred for 2 hours at 120° C. The reaction suspension was diluted with ethyl acetate and filtered. The filtrate was concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (AcOEt-hexane) to give the title compound (92 mg) having the following physical data.

Workup

filtrationfiltered
concentrationThe filtrate was concentrated under the reduced pressure
customThe residue was purified on silica gel column chromatography (AcOEt-hexane)

Sources & evidence

ORD record: ord-1c1d627ad067465f96f9378ff0f0da55
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790866B2

Reaction notes

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