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

HRID 2399607Notes

Reaction equation

HRID 2399607 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 and then ice-cooling. 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 water and ethanol, 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. temperatureice-cooling
  3. customreaction solution
  4. filtrationThe precipitate was collected by filtration
  5. washsuccessively washed with water and ethanol
  6. customair-dried

Sources & evidence

ORD record
ord-9efc51fc18df45a196b0d7ff42075c3e
Source dataset
uspto-grants-1995_09
Patent number
US05449826

Reaction notes

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