Thionyl Chloride → 5-(chloromethyl)-4-methyl-1-(propan-2-yl)-1H-imidazole hydrochloride

HRID 630127Notes

Reaction equation

HRID 630127 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH:9]([CH3:11])[CH3:10])[C:6]=1[CH2:7]O.S(Cl)([Cl:14])=O>ClCCl>[ClH:14].[Cl:14][CH2:7][C:6]1[N:5]([CH:9]([CH3:11])[CH3:10])[CH:4]=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59589489[4-methyl-1-(propan-2-yl)-1H-imidazol-5-yl]methanol

Product 1

HCID 668208845-(chloromethyl)-4-methyl-1-(propan-2-yl)-1H-imidazole hydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-methyl-1-(propan-2-yl)-1H-imidazol-5-yl]methanol (703 mg, 4.6 mmol) in anhydrous dichloromethane (40 mL) was added thionyl chloride (1.7 mL). The mixture was stirred at room temperature overnight. Dichloromethane was evaporated, and then the mixture was co-evaporated with toluene (1×20 mL). The residue was dried in vacuo, affording 5-(chloromethyl)-4-methyl-1-(propan-2-yl)-1H-imidazole hydrochloride (824 mg, 86% 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-8fe24938ba2e4a198394997495995282
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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