1-Bromodecane → 1-Decyl-2-methyl-1H-imidazole

HRID 53467

Reaktionsgleichung

Reaktionsgleichung von HRID 53467
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:8]([N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Komponenten

6

Edukt 3

HCID 81731-BromodecaneHCID 127492-MethylimidazoleHCID 14798Sodium Hydroxide

Produkt 1

HCID 27759241-Decyl-2-methyl-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 2-methylimidazole (12.3 g; 0.15 mol), 1-bromodecane (33.15 g; 0.15 mol), sodium hydroxide solution (69.5 ml. of 11.5M solution; 0.8 mol) and tetra-n-butylammonium bromide (1.95 g; 0.006 mol) in toluene (300 ml) was stirred rapidly for 3 hours at 65° C. After cooling to between 20° and 25° C., the toluene layer was separated and extracted with 5M HCl solution (150 ml). The extract neutralised with sodium bicarbonate and extracted many times into hexane. The hexane solution was dried over magnesium sulphate and evaporated to dryness to give an oil (25 g; 75% theory).

Aufarbeitung

  1. temperatureAfter cooling to between 20° and 25° C.
  2. customthe toluene layer was separated
  3. extractionextracted with 5M HCl solution (150 ml)
  4. extractionThe extract neutralised with sodium bicarbonate and extracted many times into hexane
  5. dry with materialThe hexane solution was dried over magnesium sulphate
  6. customevaporated to dryness
  7. customto give an oil (25 g; 75% theory)

Quellen und Nachweise

ORD-Eintrag
ord-c257b3c794de4fd7976632967b32723a
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620595

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