Method of obtaining substituted aminobenzhydrols

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining substituted aminobenzhydrols, which can be used as semi-products in synthesis of medications of general formula , where: R1=R3=H, R2=NH2, R4=Cl (1); R1=R3=H, R2=NH2, R4=Br (2); R1=R3=H, R2=NH2, R4=OCH3 (3); R1=R4=H, R2=NH2, R3=Cl (4); R1=H, R2=NH2, R3=Cl, R4=Cl (5); R1=NH2, R2=Cl, R3=R4=H (6); R1=NH2, , R3=R4=H (7); R1=NH2, R2=Cl, R3=H, R4=Cl (8); R1=NH2, , R3=H, R4=Cl (9); R1=NH2, R3=Cl, R2=R4=H (10); R1=NH2, , R2=R4=H (11); R1=NH2, R2=H, R3=Cl, R4=Cl (12); R1=NH2, R2=H, , R4=Cl (13), whish lies in simultaneous reduction of nitro- and carbonyl groups of respective nitrobenzphenones of general formula , where: R1=R3=H, R2=NO2, R4=Cl; R1=R3=H, R2=NO2, R4=Br; R1=R3=H, R2=NO2, R4=OCH3; R1=R4=H, R2=NO2, R3=Cl; R1=H, R2=NO2, R3=Cl, R4=Cl; R,=NO2, R2=Cl, R3=R4=H; R1=NO2, , R3=R4=H; R1=NO2, R2=Cl, R3=H, R4=Cl; R1=NO2, , R3=H, R4=Cl; R1=NO2, R3=Cl, R2=R4=H; R1=NO2, , R2=R4=H; R1=NO2, R2=H, R3=Cl, R4=Cl; R1=NO2, R2=H, , R4=Cl, reducing system Zn-NaBH4 in alcohol with molar ratio of substratum : zinc: sodium tetrahydroborate equal 1 : 3.5 : 0.25.

EFFECT: reduction of synthesis cost, reduction of time and temperature for process carrying out, increase of target products output.

1 cl, 2 tbl, 13 ex

 

The invention relates to a method for the synthesis of aromatic amino compounds, in particular the production of substituted aminobenzimidazole General formula

where R1=R3=H, R2=NH2, R4=Cl (1); R1=R3=H, R2=NH2, R4=Br (2); R1=R3=H, R2=NH2, R4=OCH3(3); R1=R4=H, R2=NH2, R3=Cl (4); R1=H, R2=NH2, R3=Cl, R4=Cl (5); R1=NH2, R2=Cl, R3=R4=H (6); R1=NH2,

,

R3=R4=H (7); R1=NH2, R2=Cl, R3=H, R4=Cl (8); R1=NH2,

,

R3=H, R4=Cl (9); R1=NH2, R3=Cl, R2=R4=H (10); R1=NH2,

,

R2=R4=H (11); R1=NH2, R2=H, R3=Cl, R4=Cl (12); R1=NH2, R2=H,

,

R4=Cl (13), which can be used as intermediates in the synthesis of pharmaceuticals (Pei Y., Lilly M., Owen D., D Sousa L., Tang X., Yu J., Nazarbaghi R., Hunter, A., Anderson C., Glasco, S., N. Ede, James I., U. Maitra, S. Chandrasekaran, W. Moos, Ghoush S.S. // J. Org. Chem., 2003, 68, No. 1, p.92) and dyes (U.S. Pat. 5026634. USA, 1991, Michio Ono, Hiroyuki Hirai, Nobutaka Onki, Kouichi Hanaki, Koki Nakamura).

The claimed compounds are:

4-amino-4'-x is orangery (1):

4-amino-4'-brombenzene (2):

4-amino-4'-methoxybenzyl (3):

4-amino-2-chlorobenzhydrol (4):

4-amino-2,4'-dichlorbenzene (5):

3-amino-4-chlorobenzhydrol (6):

,

3-amino-4-morpholinomethyl (7):

3-amino-4,4'-dichlorbenzene (8):

3-amino-4-morpholino-4'-chlorobenzhydrol (9):

5-amino-2-chlorobenzhydrol (10):

5-amino-2-morpholinomethyl (11):

5-amino-2,4'-dichlorbenzene (12):

5-amino-2-morpholino-4'-chlorobenzhydrol (13):

A method of obtaining 2,5-dimethoxy-3'-aminobenzyl based on one-step recovery nitro and carbonyl groups of the corresponding benzophenone, which consists in the catalytic hydrogenation of the substrate when used as a catalyst 10% Pd/C. the Process is carried out at a hydrogen pressure of 100 kg/cm2in ethanol, at a temperature of 130°C. for 8 hours, the product Yield is 53%. (U.S. Pat. 5026634. USA, 1991, Michio Ono, Hiroyuki Hirai, Nobutaka Onki, Kouichi Hanaki, Koki Nakamua).

The disadvantages of the known method for the synthesis of substituted aminobenzimidazole is the use of expensive palladium, high temperature and pressure, the duration of the process and low yield of the target compound.

The purpose of the invention is reducing the cost of synthesis, reducing the time and temperature of the process, higher yields of the target products.

This objective is achieved in that the reducing agent is used cheaper system reagents zinc - tetrahydridoborate sodium, the process is carried out at atmospheric pressure, a temperature of 60°C for 2 hours and a molar ratio of substrate: zinc: tetrahydridoborate sodium equal to 1:3.5:0.25, thus reducing the reaction temperature from 130°C to 60°C and to reduce the process time from 8 h to 2 h, while the yields of the target compounds are 94.8-98.5%.

The structure and purity of the target aminobenzimidazole analyzed by the method of the PMR, mass spectroscopy, melting point and elemental composition.

The invention is illustrated by the following examples.

Example 1. 4-amino-4'-chlorobenzhydrol (1)

To a suspension of 1 g (1 mol) of 4-nitro-4'-chlorobenzophenone in 20 ml of ethyl alcohol at a temperature of 20°C make 0.86 g (3.5 mol) of Zn and 0.03 g (0.25 mol) of NaBH4and lead the process for 2 h at 60°C. Hotfile revival the reaction mixture from the oxide of Zn and treat the filtrate with a solution of Hcl concentration of 0.1 mol/l to pH=7. The precipitation is filtered off and washed with 10 ml of ethyl alcohol. Obtain 0.86 g (97% of theory) of 4-amino-4'-chlorobenzhydrol - white powder, TPL 108-110°C.

Found, %: C at 66.84; H, 5.14; N, 6.02

Calculated, %: C, 66.81; H, 5.17; N, 5.99

1N PMR (DMSO-d6) δ MD: 7.51 (d, 2H, H3'H5', J=9.0), 7.30 (d, 2H, H2'H6', J=7.0), 6.96 (d, 2H, H2H6, J=8.0), 6.52 (d, 2H, H3H5, J=7.0), 5.65 (m, 1H, CH), 5.49 (m, 1H, OH), 5.05 (s, 2H, NH2).

Examples 2-13. Substituted aminobenzimidazole get analogously to example 1.

Physico-chemical characteristics of aminobenzimidazole are shown in tables 1 and 2.

The method of obtaining substituted aminobenzimidazole General formula

where R1=R3=H, R2=NH2, R4=Cl (1); R1=R3=H, R2=NH2, R4=Br (2); R1=R3=H, R2=NH2, R4=OCH3(3); R1=R4=H, R2=NH2, R3=Cl (4); R1=H, R2=NH2, R3=Cl, R4=Cl (5); R1=NH2, R2=Cl, R3=R4=H (6); R1=NH2,

R3=R4=H (7); R1=NH2, R2=Cl, R3=H, R4=Cl (8); R1=NH2,

R3=H, R4=Cl (9); R1=NH2, R3=N, R2=R4=H (10); R1=NH2,
R2=R4=H (11); R1=NH2, R2=H, R3=Cl, R4=Cl (12); R1=NH2, R2=H

R4=Cl (13), involving simultaneous recovery nitro and carbonyl groups of the respective nitrobenzophenone General formula

where R1=R3=H, R2=NO2, R4=Cl; R1=R3=H, R2=NO2, R4=Br; R1=R3=H, R2=NO2, R4=OCH3; R1=R4=H, R2=NO2, R3=Cl; R1=H, R2=NO2, R3=Cl, R4=Cl; R1=NO2, R2=Cl, R3=R4=H; R1=NO2,

R3=R4=H; R1=NO2, R2=Cl, R3=H, R4=Cl; R1=NO2,

R3=H, R4=Cl; R1=NO2, R3=N, R2=R4=H; R1=NO2,

R2=R4=H; R1=NO2, R2=H, R3=Cl, R4=Cl; R1=NO2, R2=H

R4=Cl, restoring the system Zn-NaBH4in alcohol at a molar ratio of substrate:zinc:tetrahydridoborate sodium equal to 1:3.5:0.25.



 

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FIELD: organic chemistry.

SUBSTANCE: invention relates to new method for production of compounds of general formula

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, , .

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< / BR>
< / BR>
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FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining 3,4'-diamino-4-R-benzhydrols of general formula . Where R1=Cl (1); R1=Br (2); R1= (3), which are used as semi- products in synthesis of nitrogen dyes, consisting in simultaneous reduction of nitro- and carbonyl groups of respective dinitrobenzophenons of general formula . Where: R1=Cl; R1=Br; , reduction system Zn-NaBH4 in alcohol with mole substratum ratio: zinc: sodium tetrahydroborate equals 1:6:0.5.

EFFECT: reduction of synthesis cost, reduction of time and temperature of process carrying out, increase of target product output.

1 cl, 2 tbl, 3 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for synthesis of 3,4'-diamino-4-R-benzophenones of the general formula: wherein R means Cl, Br, F, -CH3, -OCH3,

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EFFECT: improved method of synthesis.

4 tbl, 4 ex

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16 cl, 3 tbl, 7 dwg, 10 ex

FIELD: organic chemistry, agriculture, insecticides.

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EFFECT: valuable properties of compound.

5 cl, 6 tbl, 27 ex

The invention relates to biochemistry, in particular, to the use of known substituted N-(2-aminobenzyl)cyclohexylamine General formula, where R=Cl or Br, R1=H or HE, and their pharmacologically acceptable salts as an inhibitor of NO-dependent activation of soluble form of guanylate cyclase (RGC)

FIELD: chemistry.

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1 cl, 2 tbl, 3 ex

FIELD: chemistry.

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10 cl, 2 tbl, 6 ex, 5 dwg

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2 cl, 1 tbl, 14 ex

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2 cl, 2 ex

FIELD: organic chemistry.

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2 cl, 1 tbl, 9 ex

FIELD: organic chemistry, chemical technology.

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EFFECT: improved method of synthesis.

3 tbl, 4 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to methods for synthesis of 4-aminodiphenylamine, its intermediate compounds, i. e. 4-nitrodiphenylamino- and/or 4-nitrosodiphenylamino- or alkylated derivative of 4-aminodiphenylamine. Method involves the following steps: (a) interaction of aniline or its derivative and nitrobenzene in the closed zone in the presence of a mixture containing a base and oxidant comprising hydrogen peroxide in the amount from about 0.01 to about 0.60 mole of hydrogen peroxide per number of moles of nitrobenzene for synthesis of at least one intermediate compound of 4-aminodiphenylamine. Indicated oxidant and nitrobenzene are fed into the indicated closed zone simultaneously and water and aniline are removed by boiling; (b) reduction of intermediate compound to 4-aminodiphenylamine and (c) optional hydroalkylation of 4-aminodiphenylamine to yield alkylated derivative of 4-aminodiphenylamine.

EFFECT: improved method of synthesis.

10 cl, 14 tbl, 5 dwg, 17 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for preparing 4-aminodiphenylamine or its alkylated or substituted derivatives. Method involves the following steps: (a) contacting aniline or aniline derivative and nitrobenzene or nitrobenzene derivative; (b) preparing intermediate substance of 4-aminodiphenylamine by interaction of aniline or derivative of aniline and nitrobenzene or derivative of nitrobenzene in the presence of a mixture containing strong base, peroxide and interphase catalyst, or only for part of time when interaction of aniline and nitrobenzene occurs in the presence of a mixture containing strong base, air and interphase catalyst. The interphase catalyst is chosen from group of compounds determined by the formula (I): wherein R1, R2 and R3 are similar or different and chosen from any alkyl group with direct or branched chain comprising from C1 to C20; (R4)e represents hydrogen atom, for e = 0; R4 represents R1R2R3N+, for e = 1 or 2; Y represents alkyl, aryl, alkylaryl or benzyl and their substituted derivatives; Z represents substitute chosen from group consisting of hydroxyl, halogen atom and other heteroatoms; X represents anionic residue as fluoride, chloride, hydroxide, sulfate, hydrosulfate, acetate, formate, nitrate, phosphate, hydrophosphate, dihydrophosphate, oxalate, carbonate, borate, tartrate, citrate, malonate and mixture of indicated compounds wherein a means valence of anionic residue (1, 2 or 3); b and c represent whole number with value 1, 2 or 3; d represents whole number with value from 0 to 4 and wherein strong base and interphase catalyst can be similar or different; (c) reduction of intermediate substance of 4-aminodiphenylamine from step (b) to obtain 4-aminodiphenylamine or its substituted derivatives, and (d) optionally, reductive alkylation of 4-aminodiphenylamine or its substituted derivatives from step (c) to an alkylated derivative of 4-aminodiphenylamine or its substituted derivatives.

EFFECT: improved preparing method.

18 cl, 22 tbl, 16 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a solution used in synthesis of 4-aminodiphenylamine. Method involves the condensation reaction of nitrobenzene with aniline followed by catalytic hydrogenation of prepared mixture of 4-nitroso- and 4-nitrodiphenylamine tetramethylammonium salts containing aniline, potassium chloride and water. The solution contains additionally aniline tetramethylammonium salt of the formula: C6H5NHM wherein M represents tetramethylammonium cation (CH3)4N+ in the following ratio of components, wt.-%: C6H5NHM, 18.2-22.6; aniline, 52.0-64.7; water, 11.0-28.4; KCl, 1.4-1.7. Method for preparing the claimed solution used for synthesis of 4-aminodiphenylamine involves dissolving tetramethylammonium chloride in water, addition of equivalent amount of potassium hydroxide, removal of potassium chloride excess by filtration and addition of aniline to filtrate. Method for preparing 4-aminodiphenylamine by using the claimed solution involves the condensation reaction of aniline tetramethylammonium salt of the formula C6H5NHM wherein M represents tetramethylammonium cation (CH3)4N+ with nitrobenzene in aniline medium and the following distilling off water to obtain a mixture of 4-nitroso- and 4-nitrodiphenylamine tetramethylammonium salts. By termination of the condensation reaction tetramethylammonium hydroxide is removed and the remaining mixture of 4-nitroso- and 4-nitrodiphenylamine is hydrogenated catalytically to 4-aminodiphenylamine in medium consisting of aniline, toluene and water. Using the claimed solution provides increasing the yield of 4-aminodiphenylamine, and to simplify and reduce cost of the process.

EFFECT: improved method for preparing and synthesis.

4 cl, 4 ex

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