Chlorosuccinimide → 2-Chloro-4-dodecylsulfonylaniline

HRID 35795Notes

Reaction equation

HRID 35795 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-dodecylsulfonylaniline

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-dodecylsulphonylaniline (519.8 g, 1.6 moles), 1,2-dichlorethane (2.5 liters) and N-chlorosuccinimide (NCS) (110 g, 0.825 moles) was stirred at reflux for 45 minutes, then a further 60 g (0.45 moles) of NCS added. Refluxing was continued for another 45 minutes and another 53 g of NCS was added. The mixture was refluxed for another hour. The total amount of NCS used was 223 g (1.67 moles). TLC showed no starting material. The solvent was removed on the rotavapor, the residue dissolved in ethyl acetate (2 liters), washed with 3×1.5 liters of hot water, dried (MgSO4) and the solvent removed. The product was recrystallized twice from petroleum ether plus a little ethyl acetate to give 513.6 g (89%).

Workup

  1. temperatureat reflux for 45 minutes
  2. temperatureRefluxing
  3. temperatureThe mixture was refluxed for another hour
  4. customThe solvent was removed on the rotavapor
  5. dissolutionthe residue dissolved in ethyl acetate (2 liters)
  6. washwashed with 3×1.5 liters of hot water
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed
  9. customThe product was recrystallized twice from petroleum ether
  10. customa little ethyl acetate to give 513.6 g (89%)

Sources & evidence

ORD record
ord-39dafc60a85040e5987ef169e11217a0
Source dataset
uspto-grants-1995_05
Patent number
US05411841

Reaction notes

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