Iodoethane → HCID 69817507, compound

HRID 2306531Notes

Reaction equation

HRID 2306531 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[C:7]2([CH3:15])[CH3:14])([O-:3])=[O:2].[CH2:16]([I:18])[CH3:17]>>[I-:18].[CH2:16]([N+:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([CH3:15])([CH3:14])[C:8]=1[CH3:13])[CH3:17]

Participants

3

Reactant 2

HCID 6340Iodoethane2×HCID 975513H-Indole, 2,3,3-trimethyl-5-nitro-

Product 1

HCID 69817507HCID 69817507, compoundYield 53.1%

Procedure

5-Nitro-2,3,3-trimethylindole (518 mg, 2.54 mmol) and ethyl iodide (2.5 ml, 4.85 g, 31 mmol, excess) were mixed and heated to reflux for 8 hours. After cooling to room temperature the excess ethyl iodide was removed by a gentle nitrogen stream and the residue was dissolved in chloroform and filtered through a plug of silica. The silica was washed with chloroform (1 volume) and the combined filtrates were rotary evaporated to give the product as a yellow oil, (486 mg, 1.35 mmol, 53% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 hours
  3. customwas removed by a gentle nitrogen
  4. dissolutionthe residue was dissolved in chloroform
  5. filtrationfiltered through a plug of silica
  6. washThe silica was washed with chloroform (1 volume)
  7. customthe combined filtrates were rotary evaporated

Sources & evidence

ORD record
ord-b6ee575cc8b64a39b932c7da96354243
Source dataset
uspto-grants-2004_12
Patent number
US06828116B1

Reaction notes

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