4-Toluenesulfonyl chloride → 1-Tosylpyrrole

HRID 389006Notes

Reaction equation

HRID 389006 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[OH-].[Na+].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>ClC(Cl)C>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8027PyrroleHCID 14798Sodium Hydroxide

Product 1

HCID 6400871-TosylpyrroleYield 76%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Pyrrole (18 g, 0.27 mol) was added to a well-agitated suspension of NaOH (36 g, 0.9 mol. NaOH should be ground and stirred in dichloroethane for 30 min.) in 180 mL of dichloroethane. This mixture was then cooled to 0° C. and stirred for 10 min, following which a solution of 6 (57.3 g, 0.3 mol) in 150 mL of dichloroethane was added over a period of 30 min. Thirty minutes after the completion of addition, the reaction was allowed to come to room temperature and left stirring overnight. The reaction was quenched by pouring onto 600 mL of ice and water. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (3×20 mL). The combined organic extract was washed with brine to neutrality and dried over Na2SO4. Removal of the solvent in vacuo gave 7 (45.3 g, 76%) as light grey solid. This solid was subsequently purified by passing a concentrated solution in dichloromethane through an alumina column (35.4 g). 1H NMR (CDCl3, δ/ppm), 7.75 (m, 2H), 7.29 (m, 2H), 7.15 (t, 2H), 6.28 (t, 2H).

Workup

  1. additionwas added over a period of 30 min
  2. additionThirty minutes after the completion of addition
  3. customto come to room temperature
  4. waitleft
  5. stirringstirring overnight
  6. customThe reaction was quenched
  7. additionby pouring onto 600 mL of ice and water
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with dichloromethane (3×20 mL)
  10. extractionThe combined organic extract
  11. washwas washed with brine to neutrality
  12. dry with materialdried over Na2SO4
  13. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-64d696cb421c413abdf71c7ec465ce8a
Source dataset
uspto-grants-2013_02
Patent number
US08378058B2

Reaction notes

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