Diethyl Sulfate → 4'-Chloro-N-ethyl-2'-nitro-p-toluenesulfonanilide

HRID 1356660Notes

Reaction equation

HRID 1356660 reaction equation
[Na].[Cl:2][C:3]1[CH:19]=[CH:18][C:6]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1.S(OCC)(O[CH2:27][CH3:28])(=O)=O.[OH-].[Na+]>CN(C=O)C>[Cl:2][C:3]1[CH:19]=[CH:18][C:6]([N:7]([CH2:27][CH3:28])[S:8]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 69822695HCID 69822695, compound

Product 1

HCID 117031324'-Chloro-N-ethyl-2'-nitro-p-toluenesulfonanilideYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4′-chloro-2′-nitro-p-toluenesulfonanilide sodium salt (1046 g (3.00 mol)) and DMF (1100 ml), heated in an oil bath kept at 100° C., was added diethyl sulfate (733.8 g (4.50 mol)) over a period of one hour. The resulting mixture was further stirred for 1.5 hours at the same temperature to complete the reaction, and then left to cool to room temperature. A 1.5% aqueous sodium hydroxide solution was added and the mixture was stirred for one hour. The resulting solid was then filtered, washed with water, dried and recrystallized from 1450 ml of ethyl acetate to give 858 g (81%) of the title compound as pale yellow crystals.

Workup

  1. temperatureheated in an oil bath
  2. customkept at 100° C.
  3. customthe reaction
  4. waitleft
  5. stirringthe mixture was stirred for one hour
  6. filtrationThe resulting solid was then filtered
  7. washwashed with water
  8. customdried
  9. customrecrystallized from 1450 ml of ethyl acetate

Sources & evidence

ORD record
ord-8d4d4f54b98c44e8bb89d144987ba96c
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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