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Method for preparing arylamine by catalysis in aqueous phase

A water-phase medium and catalyst technology, which is applied in the preparation of amino compounds, chemical instruments and methods, and the preparation of organic compounds, and can solve problems such as limiting the scope of application of functional groups and harsh reaction conditions

Inactive Publication Date: 2010-06-02
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional synthetic method of benzimidazole is prepared by the condensation reaction of o-phenylenediamine and carboxylic acid, but harsh reaction conditions limit the scope of application of its functional group (referring to: D.W.Hein, R.J.Alhein, J.J.Leavitt, J.Am.Chem .Soc.1957, 79, 427.)

Method used

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  • Method for preparing arylamine by catalysis in aqueous phase
  • Method for preparing arylamine by catalysis in aqueous phase
  • Method for preparing arylamine by catalysis in aqueous phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: iodobenzene prepares aniline

[0034] Add 0.5 mmol (102 mg) of iodobenzene, 0.025 mmol of copper complex, 1 mmol (40 mg) of sodium hydroxide, 1 mL of 25%-28% ammonia water, and 2 mL of water into the reaction vessel. React in an oil bath at 120°C for 12 hours, and cool to room temperature. The product was extracted with ethyl acetate, concentrated under reduced pressure, and the product was purified by column chromatography. A pale yellow oily product was obtained with a yield of 83%. 1 H NMR (CDCl 3 , 400MHz) δ7.15(t, 2H), 6.76(t, 1H), 6.69(d, 2H), 3.52(s, 2H); 13 C NMR (CDCl 3 , 100MHz) δ145.9, 128.5, 117.6, 114.4. MS (EI, m / z): 93 [M + ].

Embodiment 2

[0035] Embodiment 2: p-methyl iodobenzene prepares p-toluidine

[0036] The preparation method is the same as in Example 1, except that 0.5 mmol (108.5 mg) of p-methyliodobenzene is added. A light yellow solid product was obtained with a yield of 86%. 1 H NMR (CDCl 3 , 400MHz) δ6.96(d, 2H), 6.61(d, 2H), 3.42(s, 2H), 2.24(s, 3H). 13 CNMR (CDCl 3 , 100MHz) δ143.8, 129.7, 127.7, 115.3, 20.4. MS (EI, m / z): 107 [M + ].

Embodiment 3

[0037] Embodiment 3: o-methyl iodobenzene prepares o-toluidine

[0038] The preparation method is the same as in Example 1, except that 0.5 mmol (108.5 mg) of o-methyl iodobenzene is added. A light yellow oily product was obtained with a yield of 71%. 1 H NMR (CDCl 3 , 400MHz) δ7.07-7.03(m, 2H), 6.76-6.72(m, 2H), 4.02(s, br, 2H), 2.20(s, 3H); 13 C NMR (CDCl 3 , 100MHz) δ143.0, 129.5, 126.0, 121.7, 118.0, 114.2, 16.3. MS (EI, m / z): 107 [M + ].

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Abstract

The invention provides a novel method for preparing arylamine by catalysis in aqueous phase, disclosing a primary arylamine preparation method which is safe, cheap, and environment-friendly and has atom economy by efficiently catalyzing ammonia water in aqueous phase to generate a coupling reaction with aryl halide through utilizing a water soluble coordination compound. The invention can be applied to water phase synthesis of important pharmaceutical intermediates, such as substituted benzimidazole, and the like, and chemical materials. Compared with the prior art, the method not only is suitable for wider functional groups, and has high yield, less byproducts, has simple operation, safety, low cost and less pollution.

Description

1. Technical field [0001] The present invention relates to a method for preparing aromatic amines through the coupling of halogenated aromatic hydrocarbons and ammonia water catalyzed by a coordination compound in the water phase, and a one-pot method for synthesizing substituted benzimidazoles from the halogenated aromatic hydrocarbons and ammonia water in the water phase method. 2. Background technology [0002] Aniline compounds are an important class of organic synthesis intermediates, which are widely used in medicine, pesticides, and material science. At present, domestic and foreign industries mainly adopt the method of catalytic hydrogenation of nitroaromatics to synthesize aromatic amines. (See: eg DE-OS2201528, DE-OS 3414714, US 3136818, EP 0696573). This method generally needs to be carried out under harsh conditions such as high temperature and high pressure. The equipment is expensive, the process is complicated, the operation is inconvenient, and a large numb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/08C07D213/73C07C211/52C07C211/58C07C211/47C07C211/46C07C209/10C07C225/22C07C221/00C07C217/84C07C213/02B01J31/32B01J31/28
Inventor 周向葛吴迪吴之清
Owner SICHUAN UNIV
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