Benzenesulfonyl chloride → 1-Phenylsulfonylpyrrole

HRID 873660Notes

Reaction equation

HRID 873660 reaction equation
[OH-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[C:8]1([S:14]([N:3]2[CH:7]=[CH:6][CH:5]=[CH:4]2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8027PyrroleHCID 14798Sodium Hydroxide

Product 1

HCID 1401461-PhenylsulfonylpyrroleYield 5,998.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a well-agitated suspension of sodium hydroxide (4.46 g, 111 mmol) in methylene chloride (26 mL) at 0° C. is added pyrrole (2.5 g, 0.37 mmol), and the reaction mixture is stirred for 10 min, following which a solution of benzenesulfonyl chloride (7.86 g, 0.44 mmol) in methylene chloride (5.15 mL) is slowly added, allowed to warm to room temperature and stirred overnight. The reaction is quenched by pouring into water (100 mL). The organic layer is separated, and the aqueous layer is extracted with methylene chloride three times. The combined organic extracts are water, dried with sodium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (10% ethyl acetate-hexane) provides 4.6 g (60%) of the title compound as a white solid. 1H NMR (CDCl3): δ 7.80 (m, 2H), 7.50 (m, 3H), 7.25 (m, 2H), 6.30 (m, 2H).

Workup

  1. additionis slowly added
  2. stirringstirred overnight
  3. customThe reaction is quenched
  4. additionby pouring into water (100 mL)
  5. customThe organic layer is separated
  6. extractionthe aqueous layer is extracted with methylene chloride three times
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography (10% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-7f3b6ce5651149c4b2e09283bac8e94c
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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