Pyridine → N-(5-chloroacetylamino-2-phenoxyphenyl)methanesulfonamide

HRID 441124Notes

Reaction equation

HRID 441124 reaction equation
ClCCl.[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1.N1C=CC=CC=1.[Cl:29][CH2:30][C:31](Cl)=[O:32]>O>[Cl:29][CH2:30][C:31]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)=[O:32]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 15285979N-(5-amino-2-phenoxyphenyl)methanesulfonamide

Product 1

HCID 15285980N-(5-chloroacetylamino-2-phenoxyphenyl)methanesulfonamideYield 75.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 150 ml of a dichloromethane solution containing 15.0 g of N-(5-amino-2-phenoxyphenyl)methanesulfonamide and 4.7 g of pyridine was added 6.7 g of chloroacetyl chloride under ice-cooling, followed by stirring for an hour. Water was added to the reaction solution, followed by extraction with dichloromethane. The organic layer was successively washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was recrystallized from ethyl acetate-n-hexane to give 14.4 g of N-(5-chloroacetylamino-2-phenoxyphenyl)methanesulfonamide as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with dichloromethane
  3. washThe organic layer was successively washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-663c000ef64a431a98b908c8e984c9f8
Source dataset
uspto-grants-1996_05
Patent number
US05521311

Reaction notes

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