Thionyl Chloride → 4-(chloromethyl)-1-ethyl-5-methyl-1H-imidazole hydrochloride

HRID 577080Notes

Reaction equation

HRID 577080 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

HCID 24386Thionyl ChlorideHCID 54437975(1-ethyl-5-methyl-1H-imidazol-4-yl)methanol

Product 1

HCID 668207564-(chloromethyl)-1-ethyl-5-methyl-1H-imidazole hydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (900 μL). 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

  1. customDichloromethane was evaporated
  2. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-5c6e24676e2d4a2996767b819ba58503
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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