Imidazole → 1-Dodecyl-1H-imidazole

HRID 2413846Notes

Reaction equation

HRID 2413846 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1C=CC=CC=1>[CH2:1]([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 89191-BromododecaneHCID 14798Sodium Hydroxide

Product 1

HCID 780021-Dodecyl-1H-imidazole

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 241BenzeneSolvent

Procedure

A stirred mixture of 9.96 g. of dodecyl bromide (40 mM), 5.44 g. of imidazole (80 mM), 100 ml. of 0.97N NaOH (97 mM), 100 ml. of PhH, and 336 mg. of Aliquat 336 (1 mM; methyltricaprylylammonium chloride) was refluxed for 23 h. The benzene layer was separated, washed with brine containing a little NaOH, and evaporated. The residue was purified of a little front-running and some origin impurities by quick chromatography on 150 g. of silica gel with 1:1 CH2Cl2 --EtOAc (Rf 0.35), affording 7.48 g. of single-spot material which was distilled at ca. 0.5 Torr (bp 144° C.) to give 6.97 g. of pure product (74%): NMR 7.5 (s, 1H), 7.1 (br s, 1H), 6.95 (br s, 1H), 3.95 (t, J=7 Hz, 2H), 1.85 (m, 2H), 1.3 (s, 18H), 1.0 ppm (m, 3H).

Workup

  1. additionA stirred mixture of 9.96 g
  2. customThe benzene layer was separated
  3. washwashed with brine containing a little NaOH
  4. customevaporated
  5. customThe residue was purified of a little front-running and some origin impurities by quick chromatography on 150 g
  6. customof silica gel with 1:1 CH2Cl2 --EtOAc (Rf 0.35), affording 7.48 g
  7. distillationof single-spot material which was distilled at ca. 0.5 Torr (bp 144° C.)
  8. customto give 6.97 g

Sources & evidence

ORD record
ord-2be36d4dab2f49a5ad071b90161a70a5
Source dataset
uspto-grants-1988_01
Patent number
US04719312

Reaction notes

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