Iodoethane → 3-Ethyl-1,1,2-trimethyl-1H-benzo(e)indol-3-ium Iodide

HRID 2186039

Reaction equation

HRID 2186039 reaction equation
[CH2:1]([I:3])[CH3:2].[CH3:4][C:5]1([CH3:19])[C:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH3:18]>C(#N)C>[I-:3].[CH3:4][C:5]1([CH3:19])[C:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH:10]=[CH:9][C:8]=2[N+:7]([CH2:1][CH3:2])=[C:6]1[CH3:18]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 1705302,3,3-Trimethylbenzoindolenine

Product 1

HCID 100902153-Ethyl-1,1,2-trimethyl-1H-benzo(e)indol-3-ium IodideYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl iodide (1.1 g, 7.2 mmol) was added to an acetonitrile solution (40 ml) of 1,1,2-trimethylbenz[e]indole (1) (1.0 g, 4.8 mmol, Daiichi Pure Chemicals Co., Ltd.), and then the mixture was heated under reflux for 2 days. The reaction mixture was concentrated under reduced pressure, and ether (80 ml) was added to the residue. The resulting solid was repeatedly washed with ether to obtain the title compound (2) as a dark violet solid (1.6 g, 91%). mp. 213-218° C. (decomposition).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 days
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and ether (80 ml)
  4. additionwas added to the residue
  5. washThe resulting solid was repeatedly washed with ether

Sources & evidence

ORD record
ord-9d9cbc1d84c94af69f860275d98eabac
Source dataset
uspto-grants-2002_06
Patent number
US06403625B1

Linked notes

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