Pyridine → 1,1'-(Decane-1,10-diyl)di(pyridin-1-ium) diiodide

HRID 1036576Notes

Reaction equation

HRID 1036576 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]I.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[I-:1].[I-:1].[CH2:2]([N+:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N+:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 85378Decane, 1,10-diiodo-

Product 1

HCID 2084181,1'-(Decane-1,10-diyl)di(pyridin-1-ium) diiodideYield 90%

Conditions

Temperature
65 °C

Procedure

1,10-Diiododecane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 90% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.10 (2H, d, C2&C6-H), 8.63 (1H, t, C4-H), 8.19 (2H, t, C3&C5-H), 4.60 (2H, t, C′1-CH2), 1.89 (2H, m, C′2-CH2), 1.24 (6H, m, C′3-5-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.5, 127.9, 60.6, 30.6, 28.8, 28.1, 25.2.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washthe product washed five times with dry diethyl ether
  3. customThe resulting yellow solid was isolated in a 90% yield

Sources & evidence

ORD record
ord-7e3d1ddff4c6446ba1c47586222a31a7
Source dataset
uspto-grants-2013_10
Patent number
US08546415B2

Reaction notes

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