Ethyl Acetate → N-(5-amino-2-phenoxyphenyl)methanesulfonamide

HRID 441123Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)([O-])=O.[Cl-].[NH4+].C(OCC)(=O)C>[Fe].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 52.1 g of N-(5-nitro-2-phenoxyphenyl)methanesulfonamide was added 51 ml of an aqueous solution containing 2.7 g of ammonium chloride, and then 42.5 g of an iron powder was added thereto with heating at 80° C. with stirring, followed by stirring for 2 hours. To the reaction cooled to 50° C. were added ethyl acetate and water. The insoluble substances were removed by filtration, and the filtrate was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from ethanol to give 29.6 g of N-(5-amino-2-phenoxyphenyl)methanesulfonamide.

Workup

stirringby stirring for 2 hours
temperatureTo the reaction cooled to 50° C.
customThe insoluble substances were removed by filtration
extractionthe filtrate was extracted with ethyl acetate
washThe organic layer was successively washed with water
dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-ce80da741b9c4c74aeaecd4242b118b0
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05521311

Reaction notes

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