Pyrrole → HCID 12789391, compound

HRID 1980993Notes

Reaction equation

HRID 1980993 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 12789391HCID 12789391, compoundYield 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-e6944a61f69f4c518b7220eff18726a8
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

Loading…