Thionyl Chloride → HCID 23076585, compound

HRID 2221658Notes

Reaction equation

HRID 2221658 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([CH2:8]O)[N:5]=[CH:4]1)[CH3:2].S(Cl)([Cl:12])=O>O1CCCC1>[ClH:12].[Cl:12][CH2:8][C:6]1[N:5]=[CH:4][N:3]([CH2:1][CH3:2])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18361866(1-Ethyl-1H-imidazol-4-yl)-methanol HCl

Product 1

HCID 23076585HCID 23076585, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (100 mL) of (1-ethyl-1H-imidazol-4-yl)methanol (5.80 g) in tetrahydrofuran was added thionyl chloride (14.59 g). The reaction mixture was heated under reflux for 1 hr and concentrated. Diethyl ether was added to the residue to allow crystallization, and the obtained crystals were collected by filtration, and washed with diethyl ether. The obtained crystals were recrystallized from methanol-tetrahydrofuran to give 4-chloromethyl-1-ethyl-1H-imidazole hydrochloride as colorless crystals (8.35 g, yield 100%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationconcentrated
  4. additionDiethyl ether was added to the residue
  5. customcrystallization
  6. filtrationthe obtained crystals were collected by filtration
  7. washwashed with diethyl ether
  8. customThe obtained crystals were recrystallized from methanol-tetrahydrofuran

Sources & evidence

ORD record
ord-09d422aada6a43968ca6a817561fbaf9
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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