Iodoethane → HCID 19915715, compound

HRID 1032674Notes

Reaction equation

HRID 1032674 reaction equation
[CH2:1](I)[CH3:2].[N+:4]([C:7]1[CH:26]=[CH:25][C:10]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)([O-:6])=[O:5].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:4]([C:7]1[CH:8]=[CH:9][C:10]([CH2:11][CH2:12][N:13]([CH2:1][CH3:2])[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:25][CH:26]=1)([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 19915724HCID 19915724, compound

Product 1

HCID 19915715HCID 19915715, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl iodide (0.37 g) was added dropwise to the product of part (A) (0.75 g) and potassium carbonate (0.33 g) in acetonitrile (20 ml) and the reaction mixture was heated under reflux for 18 hours. The reaction mixture was then evaporated to dryness and the residue taken up in methylene chloride, washed twice with aqueous sodium carbonate, twice with brine, then dried (Na2SO4), filtered and evaporated to dryness. The resulting oil was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 2%). The product-containing fractions were combined and evaporated to dryness to give the title compound as an oil, yield 0.47 g.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customThe reaction mixture was then evaporated to dryness
  4. washwashed twice with aqueous sodium carbonate, twice with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe resulting oil was purified by column chromatography on silica eluting with methylene chloride
  9. additioncontaining methanol (0% up to 2%)
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-e2e40e15bb864c88b2db45b1e3f523cd
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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