Hydrochloric Acid → N-(5-nitro-2-phenoxyphenyl)methanesulfonamide

HRID 441122Notes

Reaction equation

HRID 441122 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22].Cl>C(O)C>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:12]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:13]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 14798Sodium HydroxideHCID 4416401N-(2-fluoro-5-nitrophenyl)methanesulfonamide

Product 1

HCID 15285978N-(5-nitro-2-phenoxyphenyl)methanesulfonamideYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 250 ml of an aqueous solution containing 73.5 g of phenol and 31.2 g of sodium hydroxide was added 50.0 g of N-(2-fluoro-5-nitrophenyl)methanesulfonamide, followed by reflux for 5 hours. To the ice-cooled reaction solution were successively added 50 ml of 36% hydrochloric acid and 200 ml of ethanol with stirring. The precipitate was collected by filtration, successively washed with ethanol and water, and air-dried to give 52.2 g of N-(5-nitro-2-phenoxyphenyl)methanesulfonamide as yellow prisms.

Workup

  1. temperatureby reflux for 5 hours
  2. customreaction solution
  3. filtrationThe precipitate was collected by filtration
  4. washsuccessively washed with ethanol and water
  5. customair-dried

Sources & evidence

ORD record
ord-8fa888c392ec408eabe8a04e44de0be9
Source dataset
uspto-grants-1996_05
Patent number
US05521311

Reaction notes

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