Thionyl Chloride → chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride

HRID 2101482Notes

Reaction equation

HRID 2101482 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11]O.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[ClH:1].[Cl:19][CH2:11][C:7]1[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([Cl:1])[CH:15]=[C:14]([Cl:16])[CH:13]=2)[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57801498[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-methanol

Product 1

HCID 68862721chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochlorideYield 188.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-methanol (1.7 g, 6.63 mmol) was dissolved in chloroform (16 mL) and diluted with thionyl chloride (2.9 mL, 40 mmol). The reaction was warmed to reflux. After 4 h, the reaction was concentrated to yield 1.95 g of 2-chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride as a pale yellow solid (95%).

Workup

  1. temperatureThe reaction was warmed to reflux
  2. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-77be99321b5d46759c72cbffb16d90f7
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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