Methyl iodide → 4,5,6-triiodo-1,2,3,3-tetramethyl-3H-indolium iodide

HRID 508294Notes

Reaction equation

HRID 508294 reaction equation
[I:1][C:2]1[C:10]([I:11])=[C:9]([I:12])[CH:8]=[C:7]2[C:3]=1[C:4]([CH3:15])([CH3:14])[C:5]([CH3:13])=[N:6]2.I[CH3:17]>>[I-:1].[I:1][C:2]1[C:10]([I:11])=[C:9]([I:12])[CH:8]=[C:7]2[C:3]=1[C:4]([CH3:15])([CH3:14])[C:5]([CH3:13])=[N+:6]2[CH3:17]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 717360084,5,6-triiodo-2,3,3-trimethyl-3H-indole

Product 1

HCID 866953344,5,6-triiodo-1,2,3,3-tetramethyl-3H-indolium iodideYield 93.7%

Procedure

0.6 g (1.1 mmol) of 4,5,6-triiodo-2,3,3-trimethyl-3H-indole and 0.78 g (5.5 mmol) of iodomethane were heated at 30-40° C. for 20 hours in a sealed tube. The formed precipitate was filtered, and washed with small amounts of benzene and acetone to yield 350 mg of 4,5,6-triiodo-1,2,3,3-tetramethyl-3H-indolium iodide. 1H-NMR (200 MHz, DMSO-d6), δ, ppm: 8.53 (1H, s, arom.), 3.93 (3H, s, NCH3), 2.77 (3H, s, CH3), 1.60 (6H, s, C(CH3)2).

Workup

  1. filtrationThe formed precipitate was filtered
  2. washwashed with small amounts of benzene and acetone

Sources & evidence

ORD record
ord-b16949ed4fd7497ebc56c69a5d143b67
Source dataset
uspto-grants-2015_08
Patent number
US09095612B2

Reaction notes

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