Methane → HCID 11488058, compound

HRID 373299Notes

Reaction equation

HRID 373299 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14][CH2:15][CH2:16]Cl.[I-:18].[Na+].C.[IH:21]>CC(C)=O>[I:18][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14][CH2:15][CH2:16][I:21]

Participants

6

Reactant 4

HCID 297MethaneHCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 23066591,2-bis(2-chloroethoxy)-4-nitrobenzene

Product 1

HCID 11488058HCID 11488058, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2.8 g of the dichloride obtained in Example 15 and 3.8 g of anhydrous sodium iodide in 35 ml of anhydrous acetone are stirred under a nitrogen atmosphere and heated at reflux temperature for 2 days. After cooling to ambient temperature, the solution is evaporated to dryness. The solid residue is dissolved in ether and washed with a sodium thiosulfate solution to remove iodine. The organic layer is separated, dried (Na2SO4) and evaporated to dryness, and after recrystallization from hexane the title compound is produced. Yield 60%: IR 1503 cm-1 and 1349 (aromatic C-NO2); 1HNMR (CDCl3) δ7.83 (d, 1H), 7.77 (s, 1H), 7.0 (α, 1H), 4.38 (t, 4H), 3.48 (t, 4H); MS (CI, methane), m/z 464 (M+H), 492 (M+29), 504 (M+41), 336 (MH - HI).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 days
  3. customthe solution is evaporated to dryness
  4. dissolutionThe solid residue is dissolved in ether
  5. washwashed with a sodium thiosulfate solution
  6. customto remove iodine
  7. customThe organic layer is separated
  8. dry with materialdried (Na2SO4)
  9. customevaporated to dryness
  10. customafter recrystallization from hexane the title compound
  11. customis produced

Sources & evidence

ORD record
ord-b6b9806eb97f432bbaaeeed60296c803
Source dataset
uspto-grants-1992_11
Patent number
US05162525

Reaction notes

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