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

HRID 630112Notes

Reaction equation

HRID 630112 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[CH2:8]O.S(Cl)([Cl:12])=O>ClCCl>[ClH:1].[Cl:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[CH2:8][Cl:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21657108(5-chloro-1-methyl-1H-imidazol-4-yl)methanol

Product 1

HCID 668208135-chloro-4-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-chloro-1-methyl-1H-imidazol-4-yl)methanol (397 mg, 2.7 mmol) in anhydrous dichloromethane (20 mL) was added thionyl chloride (1 mL). The mixture was stirred at room temperature for 2 hours. Dichloromethane was evaporated and then co-evaporated with toluene (2×10 mL). The residue was dried in vacuo, affording 5-chloro-4-(chloromethyl)-1-methyl-1H-imidazole hydrochloride (550 mg, 99% 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-5385161c5b3b45088605459f7e606b2e
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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