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2-trifluoromethyl benzimidazole compound and preparation method thereof

A technology for trifluoromethyl benzimidazole and compound, which is applied in the field of 2-trifluoromethyl benzimidazole compound and preparation thereof, can solve the problems of inconvenient experimental operation, difficult to obtain, etc., and achieves low cost and easy availability of catalysts, and high selection of catalysts. High performance and high productivity

Active Publication Date: 2016-01-13
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] It is also reported that trifluoroiodomethane is used as trifluoromethyl reagent (JournalofFluorineChemistry, 1982,47(15):2867-2872), but trifluoroiodomethane is a gas, and the experimental operation is inconvenient
Trifluoroacetic anhydride (Indian Journal of Heterocyclic Chemistry, 2009, (4): 307-308), 2-(trifluoroacetyl) cyclohexanone (Russian Chemical Bulletin, 1999, 48 (3): 557-560), 2,2,2- Trifluoroethane thioamide (ZhurnalOrganichnoitaFarmatsevtichnoiKhimii,2006,4(1):38-40) can also be used in the synthesis of 2-trifluoromethylbenzimidazole compounds, but most trifluoromethyl reagents are special and difficult get

Method used

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  • 2-trifluoromethyl benzimidazole compound and preparation method thereof
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Embodiment 1

[0022] Embodiment 1: the synthesis of 2-trifluoromethylbenzimidazole

[0023]

[0024] o-Phenylenediamine (22mg, 0.2mmol), 1,1,1,5,5,5-hexafluoroacetylacetone (63mg, 0.3mmol), Fe(OTf) 3 (10.1mg, 0.02mmol) and N,N-dimethylformamide (1mL), react at 80°C for 24h, monitor the reaction by TLC, add 10mL of water, extract with ethyl acetate (10mL×3), combine the organic phases, and saturate Wash with brine (20ml×2), dry over anhydrous sodium sulfate, filter, concentrate under reduced pressure, and separate by column chromatography (V 石油醚 :V 乙酸乙酯 =3:1), 36.9 mg of yellow solid was obtained, and the yield was 99%. 1 HNMR (400MHz, CDCl 3 )δ=10.63(s,1H),7.89(s,1H),7.57(s,1H),7.42(s,2H); 13 CNMR (100MHz, CDCl 3 )δ=142.10, 140.53 (q, J=40.1Hz), 133.03, 125.65, 123.88, 121.18, 120.17, 117.48, 112.00, 40.85; 19 FNMR (375MHz, CDCl 3 )δ=-64.09(s,3F).

Embodiment 2

[0025] Embodiment 2: o-phenylenediamine (22mg, 0.2mmol), 1,1,1,5,5,5-hexafluoroacetylacetone (63mg, 0.3mmol), Fe(OAc) 2 (3.5mg, 0.02mmol) and N,N-dimethylformamide (1mL), react at 80°C for 24h, monitor the reaction by TLC, add 10mL of water, extract with ethyl acetate (10mL×3), combine the organic phases, and saturate Wash with brine (20ml×2), dry over anhydrous sodium sulfate, filter, concentrate under reduced pressure, and separate by column chromatography (V 石油醚 :V 乙酸乙酯 =3:1), 32.0 mg of yellow solid was obtained, and the yield was 86%.

Embodiment 3

[0026] Embodiment 3: o-phenylenediamine (22mg, 0.2mmol), 1,1,1,5,5,5-hexafluoroacetylacetone (63mg, 0.3mmol), FeCl 2 (3.3mg, 0.02mmol) and N,N-dimethylformamide (1mL), react at 80°C for 24h, monitor the reaction by TLC, add 10mL of water, extract with ethyl acetate (10mL×3), combine the organic phases, and saturate Wash with brine (20ml×2), dry over anhydrous sodium sulfate, filter, concentrate under reduced pressure, and separate by column chromatography (V 石油醚 :V 乙酸乙酯 =3:1), 30.4 mg of yellow solid was obtained, and the yield was 82%.

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Abstract

The invention relates to a 2-trifluoromethyl benzimidazole compound and a preparation method thereof. The method comprises the following steps: with an o-aryl diamine compound (I) or (II) and 1,1,1,5,5,5-hexafluoroacetylacetone as raw materials, with cheap, easily-available and low-toxicity iron salt as a catalyst, carrying out condensation, cyclization and carbon-carbon bond cleavage so as to obtain a 2-trifluoromethyl benzimidazole compound (III) or (IV). The preparation method for the 2-trifluoromethyl benzimidazole compound provided by the invention has the advantages of mild reaction conditions, low cost, environmental friendliness, high yield and applicability to industrial production.

Description

Technical field: [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a 2-trifluoromethylbenzimidazole compound and a preparation method thereof. Background technique [0002] Benzimidazole and its derivatives have bactericidal, insecticidal, antiviral and other activities, and can be used as inhibitors of nucleic acid biosynthesis. Trifluoromethyl (CF 3 ) has strong electronegativity, lipophilicity and stable C-F bond, and the introduction of trifluoromethyl group can change the polarity, acidity, lipophilicity and metabolism and chemical stability of the compound, thereby changing the biological activity of the compound. [0003] 2-Trifluoromethylbenzimidazole and its derivatives have unique biological activities and are widely used in agricultural chemicals, functional materials and pharmaceuticals. For example: benzimidazole compounds containing 2-trifluoromethylbenzamide have excellent insecticidal and bactericidal act...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/10
CPCC07D235/10
Inventor 周海峰周艳梅隋月波刘祈星范於菟
Owner CHINA THREE GORGES UNIV
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