Butyl iodide → 3-Butyl-2,4,5-trimethylthiazol-3-ium iodide

HRID 448019Notes

Reaction equation

HRID 448019 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[CH2:9]([I:13])[CH2:10][CH2:11][CH3:12]>C(#N)C>[I-:13].[CH2:9]([N+:6]1[C:5]([CH3:7])=[C:4]([CH3:8])[S:3][C:2]=1[CH3:1])[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 10962Butyl iodideHCID 616532,4,5-Trimethylthiazole

Product 1

HCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4,5-trimethylthiazole (1.3 g, 10 mmol) and n-butyl iodide (7.4 g, 40 mmol) in anhydrous acetonitrile (30 mL) was refluxed for 72 hours and then concentrated under reduced pressure to provide the crude thiazolium salt. 1H NMR (300 MHz, DMSO-d6) δ 0.95 (t, J=7 Hz, 3H), 1.39 (sextet, J=7 Hz, 2H), 1.65 (m, 2H), 2.43 (s, 6H), 2.96 (s, 3H), 4.25 (m, 2H).

Workup

  1. temperaturewas refluxed for 72 hours
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20b9fb863e514c1190cbe561ccf3576c
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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