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

HRID 630117Notes

Reaction equation

HRID 630117 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

HCID 24386Thionyl ChlorideHCID 59589441(1-ethyl-4-methyl-1H-imidazol-5-yl)methanol

Product 1

HCID 668206265-(chloromethyl)-1-ethyl-4-methyl-1H-imidazole hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

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

Sources & evidence

ORD record
ord-caefa0a20113467e942638622639e02f
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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