Thionyl Chloride → HCID 20352861, compound

HRID 372009Notes

Reaction equation

HRID 372009 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH2:14][CH2:15]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>C1C=CC=CC=1.O>[ClH:19].[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][CH2:14][CH2:15][Cl:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 54328934HCID 54328934, compound

Product 1

HCID 20352861HCID 20352861, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 241BenzeneSolvent

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. temperatureat reflux temperature
  2. additionis added
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 0.5 hour
  5. concentrationConcentration
  6. additionfollowed by the addition of cyclohexane
  7. customyields a yellow solid
  8. customRecrystallization from ethanol-ether

Sources & evidence

ORD record
ord-18bb4de0449b4a29be4165cb97521662
Source dataset
uspto-grants-1978_05
Patent number
US04088769

Reaction notes

Loading…