Chloroacetic Acid → 1-Isopropyl-2-chloromethylbenzimidazole

HRID 1189259Notes

Reaction equation

HRID 1189259 reaction equation
[CH:1]([NH:4][C:5]1[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[Cl:12][CH2:13][C:14](O)=O>>[Cl:12][CH2:13][C:14]1[N:4]([CH:1]([CH3:3])[CH3:2])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:11]=1

Participants

3

Reactant 2

HCID 300Chloroacetic AcidHCID 105587871-N-(propan-2-yl)benzene-1,2-diamine

Product 1

HCID 212484181-Isopropyl-2-chloromethylbenzimidazoleYield 38%

Procedure

The title compound was prepared in accordance with the general method of Example 191(C), from N1-isopropylbenzene-1,2-diamine (3.88 g, 25.82 mmol) and 2-chloroacetic acid (3.70 g, 39 mmol). The crude residue was purified over silicagel chromatography (prepacked 85 g silicagel column, Cyclohexane/AcOEt:70/30 as eluent) to afford 2.05 g of 2-(chloromethyl)-1-isopropyl-1H-benzo[d]imidazole (Yield: 38%) as a light brown oil.

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 85 g silicagel column, Cyclohexane/AcOEt:70/30 as eluent)

Sources & evidence

ORD record
ord-d717d595c7ab4b789b8c87a621121a87
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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