Chlorosuccinimide → 2-Chloro-4-dodecylsulfonylaniline
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
Product 1
Reagents, catalysts & solvents 1
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.