Thionyl Chloride → 2-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 896372Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:20]=[CH:19][C:8]2[N:9]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]([CH2:12]O)=[N:11][C:7]=2[CH:6]=1)=[O:4].S(Cl)([Cl:23])=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:20]=[CH:19][C:8]2[N:9]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]([CH2:12][Cl:23])=[N:11][C:7]=2[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 2-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl ester (1.00 g, 3.62 mmol) in DCM (10 mL) was added thionyl chloride (396 μL, 5.43 mmol). The solution was stirred at 0° C. for 15 min. and concentrated in vacuo to give 2-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl ester; HCl salt (1.20 g, 100%) as a white solid, which was used without further purification:

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1a3330a0aa0447b4b50cb668a69197df
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919331B2

Reaction notes

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