Thionyl Chloride → 5-(chloromethyl)-1-ethyl-4-methyl-1H-imidazole hydrochloride
Reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8]O)=[C:6]([CH3:10])[N:5]=[CH:4]1)[CH3:2].S(Cl)([Cl:13])=O>ClCCl>[ClH:13].[Cl:13][CH2:8][C:7]1[N:3]([CH2:1][CH3:2])[CH:4]=[N:5][C:6]=1[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To (1-ethyl-4-methyl-1H-imidazol-5-yl)methanol (754 mg, 5.4 mmol) in anhydrous dichloromethane (35 mL) was added thionyl chloride (2 mL). The mixture was stirred at room temperature overnight. Dichloromethane was evaporated and then co-evaporated with toluene (2×15 mL). The residue was dried in vacuo, affording 5-(chloromethyl)-1-ethyl-4-methyl-1H-imidazole hydrochloride (1.0 g, 95% yield). The product was used without further purification.
Workup
- customDichloromethane was evaporated
- customThe residue was dried in vacuo
Sources & evidence
- ORD record
- ord-30ab7a0641004095b8f0f8f98cef0712
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040538B2
Reaction notes
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