Thionyl Chloride → 4-(chloromethyl)-1-ethyl-5-methyl-1H-imidazole hydrochloride
Reaction equation
[CH2:1]([N:3]1[C:7]([CH3:8])=[C:6]([CH2:9]O)[N:5]=[CH:4]1)[CH3:2].S(Cl)([Cl:13])=O>ClCCl>[ClH:13].[Cl:13][CH2:9][C:6]1[N:5]=[CH:4][N:3]([CH2:1][CH3:2])[C:7]=1[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (1-ethyl-5-methyl-1H-imidazol-4-yl)methanol (340 mg, 2.4 mmol) in anhydrous dichloromethane (20 mL) was added thionyl chloride (9004). The mixture was stirred at room temperature for 4 hours. Dichloromethane was evaporated, and the mixture was then co-evaporated with toluene (20 mL). The residue was dried in vacuo, affording 4-(chloromethyl)-1-ethyl-5-methyl-1H-imidazole hydrochloride (450 mg, 96% yield). The product was used without further purification.
Workup
- customDichloromethane was evaporated
- customThe residue was dried in vacuo
Sources & evidence
- ORD record
- ord-cc89ecf106494109b81b39669a90c7eb
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315521B2
Reaction notes
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