P-Toluenesulfonamide → N-(p-Toluenesulfonyl)-3-pyrroline

HRID 1648476Notes

Reaction equation

HRID 1648476 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH-].[Na+].Cl[CH2:15]/[CH:16]=[CH:17]\[CH2:18]Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:11][C:1]1[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:18][CH:17]=[CH:16][CH2:15]2)(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 14798Sodium HydroxideHCID 64321151,4-Dichloro-cis-2-butene

Product 1

HCID 11138747N-(p-Toluenesulfonyl)-3-pyrrolineYield 66.9%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A 1.0 l stirred vessel having a bottom discharge valve is charged with 51.3 g (0.3 mol) of p-toluenesulphonamide, 200 ml (1.2 mol) of 6N sodium hydroxide, 400 ml of toluene and 4.44 g (15 mmol) of tetrabutyl-ammonium chloride and, at an internal temperature of 60° C., 37.5 g (0.3 mol) of cis-1,4-dichloro-2-butene are added dropwise with vigorous stirring over a period of 20 minutes, whereupon the internal temperature rises by 2° C. The mixture is stirred for another hour at 60° C. and another 2 hours at 80° C., the aqueous phase is then separated off and the organic phase is washed at 60° C. with 100 ml of 1N sulphuric acid and 2×200 ml of water. The organic phase is filtered through a fluted filter moistened with toluene into a crystallisation vessel. Upon cooling to 0° C., 44.8 g of product, melting point 128° to 130° C., are obtained. From the concentrated mother liquor (approx. 20 g), recrystallisation from 100 ml of isopropanol or 60 ml of toluene affords a further 12 to 15 g of product, melting point: 125° to 127° C. Yield: 85 to 90% of theory.

Workup

  1. additionare added dropwise
  2. stirringwith vigorous stirring over a period of 20 minutes, whereupon the internal temperature
  3. customrises by 2° C
  4. stirringThe mixture is stirred for another hour at 60° C. and another 2 hours at 80° C.
  5. customthe aqueous phase is then separated off
  6. washthe organic phase is washed at 60° C. with 100 ml of 1N sulphuric acid and 2×200 ml of water
  7. filtrationThe organic phase is filtered through
  8. filtrationa fluted filter
  9. custommoistened with toluene into a crystallisation vessel

Sources & evidence

ORD record
ord-1197b7962f9643629186643834e5592c
Source dataset
uspto-grants-1995_07
Patent number
US05436334

Reaction notes

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