N,N-diallyl-4-methylbenzenesulfonamide → N-(p-Toluenesulfonyl)-3-pyrroline

HRID 1361750Notes

Reaction equation

HRID 1361750 reaction equation
[CH2:1]([N:4]([CH2:15][CH:16]=[CH2:17])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])C=C>[PH4+].C(Cl)Cl>[C:11]1([CH3:14])[CH:10]=[CH:9][C:8]([S:5]([N:4]2[CH2:1][CH:17]=[CH:16][CH2:15]2)(=[O:6])=[O:7])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 351447N,N-diallyl-4-methylbenzenesulfonamide

Product 1

HCID 11138747N-(p-Toluenesulfonyl)-3-pyrrolineYield 99.5%

Reagents, catalysts & solvents 2

HCID 5460504PhosphoniumCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of N,N-Diallyl-4-methyl-benzenesulfonamide (251 mg, 1.0 mmol, 1.0 equiv), phosphonium catalyst (10) (30 mg, 0.025 mmol, 0.025 equiv) in CH2Cl2 (20 mL, 0.05 M) were heated under reflux for 3 h under argon. The mixture was concentred under reduced pressure. The crude product was diluted with CH2Cl2 (1 ml) and the catalyst was precipitated with Et2O (10 mL). Filtration produced the phosphonium catalyst (10) in quantitative yield (85% purity). Evaporation of the filtrate afforded pure 1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole (99.5%). Second cycle: 1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole was obtained in 98% yield and the phosphonium catalyst (10) could be recovered in quantitative yield in 83% purity. Third cycle: 1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole was obtained in 97% yield and the phosphonium catalyst (10) could be recovered in quantitative yield in 77% purity. Fourth cycle: 1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole was obtained in 97% yield and the phosphonium catalyst (10) could be recovered in quantitative yield in 68% purity. Fifth cycle: 1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole was obtained in 95% yield and the phosphonium catalyst (10) could be recovered in quantitative yield in 67% purity.

Workup

  1. temperatureunder reflux for 3 h under argon
  2. customthe catalyst was precipitated with Et2O (10 mL)
  3. filtrationFiltration
  4. customproduced the phosphonium catalyst (10) in quantitative yield (85% purity)
  5. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-a15211461f0546fd934dba04f852a387
Source dataset
uspto-grants-2011_02
Patent number
US07880037B2

Reaction notes

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