Pyrrole → 2-Phenylthiopyrrole

HRID 1980911Notes

Reaction equation

HRID 1980911 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6]1([S:12]Cl)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCOCC>[C:6]1([S:12][C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 8027PyrroleHCID 11008040Benzenesulfenyl chloride

Product 1

HCID 127893912-PhenylthiopyrroleYield 5.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyrrole (2.0 g., 30 mmoles) was dissolved in 20 ml. of ether. Benzenesulfenyl chloride (4.5 g., 30 mmoles) was added dropwise at such a rate that the purple color of the reagent was discharged. A slightly exothermic reaction was noted. After addition was complete (10 minutes), the reaction was evaporated to an oil (5.7 g.). The oil was chromatographed on approximately 180 ml. of silica gel, eluted with ethyl acetate-1/hexane-7. Middle fractions, evaporated to dryness, afforded 2-phenylthiopyrrole (300 mg.).

Workup

  1. customA slightly exothermic reaction
  2. additionAfter addition
  3. custom(10 minutes)
  4. customthe reaction was evaporated to an oil (5.7 g.)
  5. customThe oil was chromatographed on approximately 180 ml
  6. washof silica gel, eluted with ethyl acetate-1/hexane-7
  7. customMiddle fractions, evaporated to dryness

Sources & evidence

ORD record
ord-1f4fe77593e841f1b8027829908e738d
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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