Water → HCID 54328934, compound

HRID 372008Notes

Reaction equation

HRID 372008 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH2:14][C:15](OCC)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH2:14][CH2:15][OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18349772HCID 18349772, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54328934HCID 54328934, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-benzyl-2-(2-carbethoxyethyl)imidazole (5.2 g) in dry ether (150 ml) is added, dropwise, to a stirred suspension of aluminium lithium hydride (1.0 g) in dry ether (150 ml) at gentle reflux. The suspension is subsequently heated under reflux for two hours, and then cooled during the successive addition of water (1 ml), 15% sodium hydroxide (1 ml) and water (3 ml). After heating under reflux for 0.5 hour and filtration, the insoluble solid is extracted with hot methanol (3 × 100 ml). The combined organic extracts are concentrated under reduced pressure and the residue dissolved in 2N hydrochloric acid. Following extraction with chloroform, the solution is basified with solid potassium carbonate. Chloroform extracts of the basic solution are dried over sodium sulphate and concentrated under reduced pressure, affording 1-benzyl-2-(3-hydroxypropyl) imidazole as a colourless viscous liquid (4.6 g). The carbinol (4.4 g) is dissolved in benzene (40 ml) and added to thionyl chloride (20 ml) at reflux temperature. After complete addition, water (four drops) is added and the mixture is heated under reflux for 0.5 hour. Concentration followed by the addition of cyclohexane yields a yellow solid. Recrystallization from ethanol-ether yields 1-benzyl-2-(3-chloropropyl)imidazole hydrochloride, m.p. 162°-164° C.

Workup

  1. temperatureThe suspension is subsequently heated
  2. temperatureunder reflux for two hours
  3. temperatureAfter heating
  4. temperatureunder reflux for 0.5 hour
  5. filtrationfiltration
  6. extractionthe insoluble solid is extracted with hot methanol (3 × 100 ml)
  7. concentrationThe combined organic extracts are concentrated under reduced pressure
  8. dissolutionthe residue dissolved in 2N hydrochloric acid
  9. extractionextraction with chloroform
  10. dry with materialChloroform extracts of the basic solution are dried over sodium sulphate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ace608089418465e9d4781dc564b8141
Source dataset
uspto-grants-1978_05
Patent number
US04088769

Reaction notes

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