Chlorosuccinimide → 2-Chloro-4-dodecylsulfonylaniline

HRID 1378281Notes

Reaction equation

HRID 1378281 reaction equation
[CH2:1]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Cl:23]N1C(=O)CCC1=O>ClCCCl>[Cl:23][C:21]1[CH:22]=[C:16]([S:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:15])=[O:14])[CH:17]=[CH:18][C:19]=1[NH2:20]

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide4×HCID 32561164-Dodecylsulfonylaniline

Product 1

HCID 108613032-Chloro-4-dodecylsulfonylanilineYield 173%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A stirred mixture of 4-dodecylsulfonylaniline (519.6 g 1.6 moles), 1,2-dichloroethane (2.5 liters) and N-chlorosuccinimide (110 g 0.825 moles) was heated under reflux for 45 minutes. A further 60 g (0.45 moles) of N-chlorosuccinimide was added and heating was continued for 45 minutes. A further 53 g of N-chlorosuccinimide (0.40 moles) was added and heating was maintained for another hour. The total amount of N-chlorosuccinimide was used 223 g (1.67 moles). TLC showed no starting material. The solvent was removed on the rotovapor and the residue was dissolved in ethyl acetate (2 liters). The solution was washed with 3×15 liters of hot water, then it was dried over magnesium sulfate and the solvent was removed. The product was recrystalized twice from petroleum ether (bp 60°-80° C.) containing a little ethyl acetate to give 513.6 g (89%) of pure material.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 45 minutes
  3. temperatureheating
  4. temperatureheating
  5. temperaturewas maintained for another hour
  6. customThe solvent was removed on the rotovapor
  7. dissolutionthe residue was dissolved in ethyl acetate (2 liters)
  8. washThe solution was washed with 3×15 liters of hot water
  9. dry with materialit was dried over magnesium sulfate
  10. customthe solvent was removed
  11. customThe product was recrystalized twice from petroleum ether (bp 60°-80° C.)
  12. additioncontaining a little ethyl acetate

Sources & evidence

ORD record
ord-7358ce1a0b9d4148b9ebc263de22532c
Source dataset
uspto-grants-1997_09
Patent number
US05667946

Reaction notes

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