Hydrochloric Acid → HCID 69001217, compound

HRID 1786098Notes

Reaction equation

HRID 1786098 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([Li])CCC.Cl.Cl[CH2:17][C:18]1[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=1.Cl>O1CCCC1>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:17][C:18]2[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7219IndeneHCID 27954062-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 178418339Butyllithium

Product 1

HCID 69001217HCID 69001217, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 17.4 ml of indene (0.1497 mol) in 150 ml of tetrahydrofuran (THF) was cooled to −60° C. and 61.8 ml of n-butyllithium (2M in hexane, 0.136 mol) were subsequently added while stirring. The mixture was allowed to warm to room temperature while stirring for 3 h and 5 g (0.0299 mol) of 2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride was then added while stirring. The mixture was then stirred for a further 12 hours and hydrolyzed with 400 ml of dilute hydrochloric acid, the organic phase was separated off and the aqueous phase was extracted once with ethyl acetate. The aqueous phase was then neutralized with aqueous ammonia solution and extracted 3 times with 80 ml each time of dichloromethane. The organic phases were combined and dried over magnesium sulfate. After the magnesium sulfate had been filtered off, the solvent was distilled off. The crude product was purified by column chromatography using a mixture of hexane:ethyl acetate=1:1 and then the percentage of ethyl acetate slowly increased. Thus 4.82 g of 2-(1H-inden-3-ylmethyl)-1-methyl-1H-imidazole were obtained (77%).

Workup

  1. stirringwhile stirring for 3 h
  2. stirringwhile stirring
  3. customthe organic phase was separated off
  4. extractionthe aqueous phase was extracted once with ethyl acetate
  5. extractionextracted 3 times with 80 ml each time of dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter the magnesium sulfate had been filtered off
  8. distillationthe solvent was distilled off
  9. customThe crude product was purified by column chromatography
  10. additiona mixture of hexane
  11. temperatureethyl acetate=1:1 and then the percentage of ethyl acetate slowly increased

Sources & evidence

ORD record
ord-fa8097b807c14de7b81d4f21f81fc12b
Source dataset
uspto-grants-2009_03
Patent number
US07507688B2

Reaction notes

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