2-Chloro-4-dodecylsulfonylaniline → HCID 70346894, compound

HRID 581393Notes

Reaction equation

HRID 581393 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11](=[O:13])[N:10]([CH:14]([C:20](OCC)=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])(=[O:35])=[O:34])=[CH:29][C:28]=1[Cl:48]>C1(C)C(C)=CC=CC=1>[Cl:48][C:28]1[CH:29]=[C:30]([S:33]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])(=[O:35])=[O:34])[CH:31]=[CH:32][C:27]=1[NH:26][C:20](=[O:21])[CH:14]([N:10]1[C:11](=[O:13])[CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:25])[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 108613032-Chloro-4-dodecylsulfonylanilineHCID 70345177HCID 70345177, compound

Product 1

HCID 70346894HCID 70346894, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
70 °C

Procedure

Diethyl 2-(3-benzyl-2,5-dioxo-1,3-diazolidin-1-yl)-malonate (19.3 g, 55.5 mmol) and (4-amino-3-chloro-phenyl)dodecylsulphone (20.0 g,56.0 mmol) were added to xylene (100 ml) and refluxed under Dean and Stark conditions for 80 hr, occasionally removing a small amount of distillate and replenishing the solvent as necessary. The reaction was followed by TLC (1:2 ethyl acetate:60-80° C. petroleum ether), the Rf of the product being between that of the two starting materials. The xylene was removed on the rotary evaporator and the residual yellowish oil stirred with 60-80° C. petroleum ether (100 ml), allowed to settle and decanted from the oil. This removed some front-running impurities. On standing the oil solidified to a crystalline mass which was crystallized from toluene and petrol to give a white solid, 17.0 g, 46%.

Workup

  1. temperaturerefluxed under Dean and Stark conditions for 80 hr
  2. customoccasionally removing a small amount of distillate
  3. customwas followed by TLC (1:2 ethyl acetate:60-80° C. petroleum ether)
  4. customThe xylene was removed on the rotary evaporator
  5. customdecanted from the oil
  6. customThis removed some front-running impurities
  7. customwas crystallized from toluene and petrol
  8. customto give a white solid, 17.0 g, 46%

Sources & evidence

ORD record
ord-7735ef3816d04c27b94ed55b789cf683
Source dataset
uspto-grants-1999_07
Patent number
US05919969

Reaction notes

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