Methyl iodide → HCID 86633418, compound

HRID 2382619Notes

Reaction equation

HRID 2382619 reaction equation
[I-:1].[CH3:2][C:3]1[SH+:4][CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1.CI>CO>[IH:1].[I-:1].[CH3:2][C:3]1[SH+:4][CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 86628029HCID 86628029, compound

Product 1

HCID 86633418HCID 86633418, compoundYield 121.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl-thioninium iodide (0.50 g, 1.22 mmol) was dissolved in methanol (20 cm3) and methyl iodide (1.90 g, 13.37 mmol) was added while stirring. The mixture was heated at reflux for 18 hours before additional methyl iodide (0.42 g, 6.69 mmol) was added and the mixture was once again heated to reflux and stirred for 8 hours. The mixture was cooled to room temperature, giving a solid that was filtered and washed with methanol to yield the title compound (0.30 g, 46%) as bronze green solid. δH (250 MHz; DMSO): 7.82 (2H, d, J=8.5, ArH), 7.42 (4H, s, ArH), 3.34 (12H, s, CH3). δC (62.9 MHz; DMSO): 153.8 (ArC), 137.9 (ArC), 134.9 (ArC), 133.5 (ArC), 119.1 (ArC), 118.8 (ArC), 106.9 (ArC), 106.6 (ArC), 41.1 (NCH3).

Workup

  1. temperatureThe mixture was heated
  2. additionwas added
  3. temperaturethe mixture was once again heated
  4. temperatureto reflux
  5. stirringstirred for 8 hours
  6. customgiving a solid
  7. filtrationthat was filtered
  8. washwashed with methanol

Sources & evidence

ORD record
ord-4d87bbe6ae9441b9846f98ada02878ae
Source dataset
uspto-grants-2012_09
Patent number
US08263589B2

Reaction notes

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