4-Toluenesulfonyl chloride → 1-Tosylpyrrole

HRID 345949Notes

Reaction equation

HRID 345949 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27]>C1COCC1>[S:26]([N:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8027PyrroleHCID 14798Sodium HydroxideHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 6400871-TosylpyrroleYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 1-liter three-neck flask, 8.65 cm3 of freshly distilled pyrrole (125 mmoles) was introduced together with 100 cm3 of THF and 1 cm3 of a 40% aqueous solution of tetrabutylammonium hydroxide. 125 cm3 of a 50% aqueous NaOH solution was added and the mixture was then vigorously stirred. After 5 minutes, a solution of 38 g of tosylchloride (200 mmoles) in 100 cm3 of THF was dropwise added. The obtained adduct was maintained under stirring until the temperature reached a maximum and then again during some 30 minutes more. After decantation, the aqueous layer was extracted with ethyl acetate, and the combine organic layer was concentrated under reduced pressure. The residue was dissolved in dichloromethane, washed with water, dried over magnesium sulfate and evaporated. 27 g of a white solid compound was obtained (1) (M=221, yield: 97.6%). Recrystallization in methanol. F (° C)=92. Elemental analysis: calc.: C 59.73; H 4.98; N 6.33; found: C 59.59; H 4.67; N 6.32. NMR: (CDCl3) ppm 7.7 d J(Hz) 8 2H; 7.2 4H; 6.25 2H; 2.33 s 3H.

Workup

  1. temperatureThe obtained adduct was maintained
  2. stirringunder stirring until the temperature
  3. waitagain during some 30 minutes more
  4. extractionAfter decantation, the aqueous layer was extracted with ethyl acetate
  5. concentrationthe combine organic layer was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-9ee9a0da3aee4b95b4aac853ab48a857
Source dataset
uspto-grants-1991_10
Patent number
US05059694

Reaction notes

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