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

HRID 53467

Reaction equation

HRID 53467 reaction equation
[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]

Participants

6

Reactant 3

HCID 81731-BromodecaneHCID 127492-MethylimidazoleHCID 14798Sodium Hydroxide

Product 1

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

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c257b3c794de4fd7976632967b32723a
Source dataset
uspto-grants-1997_04
Patent number
US05620595

Linked notes

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