Thionyl Chloride → HCID 23076585, compound
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe reaction mixture was heated
- temperatureunder reflux for 1 hr
- concentrationconcentrated
- additionDiethyl ether was added to the residue
- customcrystallization
- filtrationthe obtained crystals were collected by filtration
- washwashed with diethyl ether
- 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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