Iodoethane → 4778-76-1

HRID 2399762Notes

Reaction equation

HRID 2399762 reaction equation
[OH-].[K+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([OH:10])=[O:9].[CH2:11](I)[CH3:12]>CS(C)=O>[CH2:11]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]([OH:10])=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 12473Pyrrole-2-Carboxylic AcidHCID 14797Potassium Hydroxide

Product 1

HCID 154425984778-76-1Yield 78.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under nitrogen, a suspension of 50 g (0.9 mol) of pulverized KOH in 440 ml of anhydrous DMSO was treated with 20 g (0.18 mol) of pyrrole-2-carboxylic acid (Aldrich); this mixture was cooled in ice and treated with 28 ml (0.36 mol of ethyl iodide. The reaction was allowed to warm to ambient temperatures and stir overnight prior to concentration in vacuo. The residue was dissolved in 125 ml of water and the pH adjusted to 4 with aqueous HCl. The product was extracted with methylene chloride, dried (MgSO4), and concentrated in vacuo to give 19.6 g (78%) of colorless material: mp 77°-78° C.; NMR (DMSO-d6) δ 1.23(t, J=7 Hz, 3H), 4.29(q, J=7 Hz, 2H), 6.06(dd, J=3 and 1 Hz, 1H), 7.10 (t, J=2 Hz, 1H).

Workup

  1. temperaturethis mixture was cooled in ice
  2. temperatureto warm to ambient temperatures
  3. concentrationto concentration in vacuo
  4. dissolutionThe residue was dissolved in 125 ml of water
  5. extractionThe product was extracted with methylene chloride
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-686a9509ccd54bbf93986e223e0156e7
Source dataset
uspto-grants-1995_09
Patent number
US05451592

Reaction notes

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