Chloroacetic Acid → 2-(chloromethyl)-5-fluoro-1-methyl-1H-benzo[d]imidazole

HRID 334744Notes

Reaction equation

HRID 334744 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:8][CH3:9])=[CH:6][CH:7]=1.[Cl:11][CH2:12][C:13](O)=O>>[Cl:11][CH2:12][C:13]1[N:8]([CH3:9])[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[N:10]=1

Participants

3

Reactant 2

HCID 300Chloroacetic AcidHCID 199648134-Fluoro-N1-methylbenzene-1,2-diamine

Product 1

HCID 436599262-(chloromethyl)-5-fluoro-1-methyl-1H-benzo[d]imidazoleYield 8%

Procedure

The title compound was prepared in accordance with the general method of Example 191(C), from 4-fluoro-N1-methylbenzene-1,2-diamine (2.5 g, 17.84 mmol) and 2-chloroacetic acid (2.50 g, 27 mmol). The crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, Cyclohexane/AcOEt: 60/40 as eluent) to afford 277 mg of 2-(chloromethyl)-5-fluoro-1-methyl-1H-benzo[d]imidazole (Yield: 8%) as a semi-solid.

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, Cyclohexane/AcOEt: 60/40 as eluent)

Sources & evidence

ORD record
ord-bba5b47bc2c74a39b07b48264b877593
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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