Propargyl bromide → HCID 22254467, compound

HRID 434006Notes

Reaction equation

HRID 434006 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[OH-].[Na+].[CH3:7][O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:24][CH2:25][OH:26])[C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:23]=1.C(Cl)(Cl)Cl.CO>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[CH3:7][O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:24][CH2:25][O:26][CH2:3][C:2]#[CH:1])[C:13]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:23]=1

Participants

8

Reactant 4

HCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 21584188Chloroform methanolHCID 22254498HCID 22254498, compound

Product 1

HCID 22254467HCID 22254467, compoundYield 99.6%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Propargyl bromide (10.0 ml, 89.8 mmol, 80% in toluene) and benzyltrimethylammonium chloride (0.60 g, 3.2 mmol) were dissolved in dichloromethane (130 ml). The solution was treated with sodium hydroxide (130 ml, 50% w/w in water). 2-[2-(2-Methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethanol (20.0 g, 73.7 mmol) was added and the mixture was vigorously stirred for 18 hours. Thin layer chromatography (9/1 chloroform/methanol) indicated complete conversion. The mixture was diluted with water (200 ml) and the phases were separated. The aqueous fraction was extracted with additional dichloromethane (3×150 ml). The combined organic fractions were washed with brine (100 ml), dried (Na2SO4), filtered and concentrated to yield 22.7 g of 2-(2-methoxyethyl)-1-[2-(prop-2-ynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline as an orange solid.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous fraction was extracted with additional dichloromethane (3×150 ml)
  3. washThe combined organic fractions were washed with brine (100 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59beacfdd1264429bb31e1513385ad5b
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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