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

HRID 2399608Notes

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, and the precipitate was filtered. After extraction 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.
filtrationthe precipitate was filtered
extractionAfter extraction 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-da8e8c279eaa4199b5b89d106df1c397
Source dataset: uspto-grants-1995_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05449826

Reaction notes

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