Chloroacetic Acid → 1H-Benzimidazole, 2-(chloromethyl)-1-(2-phenylethyl)-

HRID 334736Notes

Reaction equation

[CH2:1]([NH:9][C:10]1[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:17][CH2:18][C:19](O)=O>>[Cl:17][CH2:18][C:19]1[N:9]([CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]=1

Participants

Reactant 2

HCID 300Chloroacetic Acid

HCID 2317489HCID 2317489, compound

Product 1

HCID 45594871H-Benzimidazole, 2-(chloromethyl)-1-(2-phenylethyl)-Yield 61.6%

Procedure

The title compound was prepared in accordance with the general method of Example 191(C), from N1-phenethylbenzene-1,2-diamine (2.57 g, 12.11 mmol) and 2-chloroacetic acid (1.70 g, 18 mmol). The crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, Cyclohexane/AcOEt: from 80/20 to 70/30 as eluent) to afford 2.02 g of 2-(chloromethyl)-1-phenethyl-1H-benzo[d]imidazole (Yield: 61%) as a white crystalline solid.

Workup

customThe crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, Cyclohexane/AcOEt: from 80/20 to 70/30 as eluent)

Sources & evidence

ORD record: ord-ea6b36f70dd7410392f5ecfd2c6e0b3c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883826B2

Reaction notes

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