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

HRID 562876Notes

Reaction equation

HRID 562876 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 6344DichloromethaneSolvent

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 concentrated 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.

Workup

  1. temperatureunder reflux for 3 h under argon
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionThe crude product was diluted with CH2Cl2 (1 ml)
  4. customthe catalyst was precipitated with Et2O (10 mL)
  5. filtrationFiltration
  6. customproduced the phosphonium catalyst (10) in quantitative yield (85% purity)
  7. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-b5277b80aa0e4bbaa26c63dab7b8a65b
Source dataset
uspto-grants-2011_11
Patent number
US08067440B2

Reaction notes

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