Iodoethane → HCID 67262703, compound

HRID 252792Notes

Reaction equation

HRID 252792 reaction equation
[Br:1][C:2]1[C:3](C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH3:12].[CH2:14]([I:16])[CH3:15].[C:17](#N)C>>[I-:16].[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N+:7]([CH2:14][CH3:15])=[C:6]([CH3:11])[C:5]2([CH3:12])[CH3:17]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 6342AcetonitrileHCID 67262654HCID 67262654, compound

Product 1

HCID 67262703HCID 67262703, compoundYield 87%

Procedure

To a 250 mL flask were added bromotrimethylindole 2 (12 g, 50.4 mmol), acetonitrile (25 mL) and ethyl iodide (20 mL). The mixture was heated at reflux under argon for 40 h. The bulk of the volatile components were removed by distillation. The residue was triturated with ether (100 mL) to give a powder. The solid was filtered off, washed with ether (2×50 mL) and dried under high vacuum to afford 3 as a solid (17.3 g, 87%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under argon for 40 h
  3. customThe bulk of the volatile components were removed by distillation
  4. customThe residue was triturated with ether (100 mL)
  5. customto give a powder
  6. filtrationThe solid was filtered off
  7. washwashed with ether (2×50 mL)
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-aa3b3278289346bea081537f7c45de1b
Source dataset
uspto-grants-2011_01
Patent number
US07868157B2

Reaction notes

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