Water → HCID 11746243, compound

HRID 2302223Notes

Reaction equation

HRID 2302223 reaction equation
[C:1]1(C)[C:2]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[OH-].[Na+].O.Cl[CH2:16]Cl.[C:18]1(C)[CH:23]=CC=[CH:20][CH:19]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:5]1([CH3:16])[CH:6]=[CH:1][C:2]([S:7]([N:10]2[CH2:20][CH2:19][CH:18]=[CH:23]2)(=[O:8])=[O:9])=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6344DichloromethaneHCID 69242-MethylbenzenesulfonamideHCID 14798Sodium Hydroxide

Product 1

HCID 11746243HCID 11746243, compound

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Conditions

Temperature
40 °C

Procedure

1.37 kg (8.0 mol) of toluenesulphonamide in 6 l of toluene are introduced into a further 20 l HC4 vessel having a distillation bridge. The mixture is treated with 3.2 kg of 45% strength sodium hydroxide solution, 0.8 l of water and 130.5 g of tetrabutylammonium hydrogensulphate, heated to a maximum internal temperature of 40° C. and vacuum is applied. The previously obtained dichloromethane solution (15.21) is then added dropwise in the course of 1.5 hours and the dichloromethane is removed by distillation at 450 mbar at the same time (bath temperature: 60° C.). During the distillation, foam formation takes place. At the end, a solution with an internal temperature of 33-40° C. is present. After completion of the addition, further dichloromethane is removed by distillation until distillate barely still passes over (time: about 85 minutes; internal temperature 40° C. with a bath temperature of 60° C. at the end). The vessel contents are then transferred whilst still warm to a separating funnel and the vessel is rinsed at 50° C. with 5 l of water and 2 l of toluene. Before the phase separation, the solid constituents in the intermediate phase are filtered off with suction and washed with 0.5 l of toluene. The organic phase is washed with 2.4 l of water with stirring, separated off and evaporated to dryness in a rotary evaporator. The solid residue (1758 g) is suspended in 1.6 l of methanol at a bath temperature of 50° C., the suspension is transferred to a 10 l flask having a plane-ground joint and the flask is rinsed with 2.4 l of diisopropyl ether. The mixture is warmed to reflux temperature (59° C.) and stirred for a further 30 minutes under reflux. The suspension is cooled to 0° C., stirred at 0° C. for 1 hour, filtered off with suction and washed with 0.8 l of a cold mixture of methanol/diisopropyl ether (1:1.5). The crystallizate is dried at 50° C./400 mbar under a nitrogen atmosphere.

Workup

  1. customthe dichloromethane is removed by distillation at 450 mbar at the same time (bath temperature: 60° C.)
  2. distillationDuring the distillation, foam formation
  3. customwith an internal temperature of 33-40° C.
  4. additionAfter completion of the addition, further dichloromethane
  5. customis removed by distillation until distillate
  6. customabout 85 minutes
  7. custominternal temperature 40° C.
  8. customtemperature of 60° C.
  9. temperaturestill warm to a separating funnel
  10. washthe vessel is rinsed at 50° C. with 5 l of water and 2 l of toluene
  11. customBefore the phase separation
  12. filtrationthe solid constituents in the intermediate phase are filtered off with suction
  13. washwashed with 0.5 l of toluene
  14. washThe organic phase is washed with 2.4 l of water
  15. customseparated off
  16. customevaporated to dryness in a rotary evaporator
  17. customThe solid residue (1758 g) is suspended in 1.6 l of methanol at a bath
  18. customtemperature of 50° C., the suspension is transferred to a 10 l flask
  19. washthe flask is rinsed with 2.4 l of diisopropyl ether
  20. temperatureThe mixture is warmed
  21. temperatureto reflux temperature (59° C.)
  22. stirringstirred for a further 30 minutes
  23. temperatureunder reflux
  24. temperatureThe suspension is cooled to 0° C.
  25. stirringstirred at 0° C. for 1 hour
  26. filtrationfiltered off with suction
  27. washwashed with 0.8 l of a cold mixture of methanol/diisopropyl ether (1:1.5)
  28. customThe crystallizate is dried at 50° C./400 mbar under a nitrogen atmosphere

Sources & evidence

ORD record
ord-f77e3f627a5447feaa9b534b823da14b
Source dataset
uspto-grants-2002_08
Patent number
US06432948B1

Reaction notes

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