Acetic Acid → N-(5-chloroacetylamino-4-nitro-2-phenoxyphenyl)methanesulfonamide

HRID 441125Notes

Reaction equation

C(O)(=O)C.[Cl:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:15]=1)=[O:8].[N+:28]([O-])([OH:30])=[O:29]>O>[Cl:5][CH2:6][C:7]([NH:9][C:10]1[C:11]([N+:28]([O-:30])=[O:29])=[CH:12][C:13]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH:15]=1)=[O:8]

Participants

Conditions

Temperature: 90 °C

Procedure

To 71 ml of an acetic acid solution containing 14.0 g of N-(5-chloroacetylamino-2-phenoxyphenyl)methanesulfonamide was added 4.4 g of 60% nitric acid with heating at 90° C. with stirring, followed by stirring for 20 minutes. Water was added to the reaction solution of which temperature was allowed to return to room temperature. The precipitate was collected by filtration and recrystallized from ethanol-n-hexane to give 9.3 g of N-(5-chloroacetylamino-4-nitro-2-phenoxyphenyl)methanesulfonamide as yellow needles.

Workup

stirringby stirring for 20 minutes
customto return to room temperature
filtrationThe precipitate was collected by filtration
customrecrystallized from ethanol-n-hexane

Sources & evidence

ORD record: ord-6958aaae077346bab9c4d1392ab74871
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05521311

Reaction notes

Loading…