Iodoethane → HCID 21459526, compound

HRID 1590569Notes

Reaction equation

HRID 1590569 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[Br:7][C:8]1[NH:9][C:10]([Br:16])=[C:11]([Br:15])[C:12]=1[C:13]#[N:14].C(I)C>O1CCCC1.O>[Br:7][C:8]1[N:9]([CH2:1][CH3:2])[C:10]([Br:16])=[C:11]([Br:15])[C:12]=1[C:13]#[N:14]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10471741HCID 10471741, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459526HCID 21459526, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (0.75 g, 6.7 mmol) is added in portions at room temperature to a solution of 2,4,5-tribromopyrrole-3-carbonitrile (2.0 g, 6.1 mmol) in anhydrous tetrahydrofuran (20 mL). After 30 minutes, ethyl iodide (1.04 g, 6.7 mmol) is added dropwise. The reaction solution is stirred at room temperature for 30 minutes and then refluxed for 90 minutes. The mixture is cooled, diluted with water and extracted with ethyl acetate. The organic layer is washed with water and saturated sodium chloride and dried (Na2SO4). Evaporation of the solvent and crystallization from ether-hexanes gives a solid which is further purified by flash column chromatography on silica gel, packed with methylene chloride and eluted with 3% ethyl acetate in methylene chloride. The analytically pure sample is finally crystallized from methylene chloridehexanes as a white solid (1.55 g); mp 108.5°-109.5° C.

Workup

  1. temperaturerefluxed for 90 minutes
  2. temperatureThe mixture is cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water and saturated sodium chloride
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent and crystallization from ether-hexanes
  7. customgives a solid which
  8. customis further purified by flash column chromatography on silica gel
  9. washeluted with 3% ethyl acetate in methylene chloride
  10. customThe analytically pure sample is finally crystallized from methylene chloridehexanes as a white solid (1.55 g)

Sources & evidence

ORD record
ord-b1710a5508494a86928aa42b41ec02ef
Source dataset
uspto-grants-1993_04
Patent number
US05204332

Reaction notes

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