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

HRID 508291Notes

Reaction equation

HRID 508291 reaction equation
[I:1][C:2]1[C:10](I)=[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[CH:10]=[C:9]([I:12])[CH:8]=[C:7]2[C:3]=1[C:4]([CH3:14])([CH3:15])[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 866953314,6-diiodo-1,2,3,3-tetramethyl-3H-indolium iodide

Procedure

1.05 g (2.5 mmol) of 4,5,6-triiodo-2,3,3-trimethyl-3H-indole and 2 mL of iodomethane were heated at 45° C. for 6 hours in a sealed tube. The formed precipitate was filtered, washed with acetone. Yield: 900 mg. 1H-NMR (300 MHz, DMSO-d6), δ, ppm: 8.37 (2H, d, 5.4 Hz, arom.), 3.92 (3H, s, NCH), 2.79 (3H, s, CH3), 1.61 (6H, s, C(CH3)2).

Workup

  1. filtrationThe formed precipitate was filtered
  2. washwashed with acetone

Sources & evidence

ORD record
ord-c6cf372ea4e64ce69ada8f3eac003624
Source dataset
uspto-grants-2015_08
Patent number
US09095612B2

Reaction notes

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