Method for preparing 3,4'-diamino-4-r-benzophenones

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,

that are used as intermediate product in synthesis of azo dyes useful for staining protein fibers and possessing the unique indices of thermal stability. Method involves steps for nitration reaction of substituted benzophenones with potassium nitrate in concentrated H2SO4, nucleophilic replacing halogen (wherein R means Cl) in interaction with O- and N-nucleophilic compounds in dimethylsulfoxide (DMSO) medium in the presence of K2CO3 and reduction of 3,4'-dinitro-4-R-benzophenones. The nitration reaction of synthesized benzophenones is carried out at temperature 20oC for 5 h in the mole ratio 4'-nitro-4-R-benzophenone : KNO3 = 1.0:1.15. Nucleophilic replacing halogen is carried out at temperature 40-60oC for 1-5 h in the mole ratio substrate : nucleophilic compound = 1.0:1.05, and reduction of dinitrobenzophenones is carried out with SnCl2 x 2H2O in 18% HCl medium, in the mole ratio 3,4'-dinitro-4-R-benzophenone : SnCl2 x 2H2O = 1:6, at temperature 20oC for 0.15 h. Invention provides decreasing cost of synthesis, reducing time and temperature in carrying out the process, enhancing purity and yield of end products.

EFFECT: improved method of synthesis.

4 tbl, 4 ex

 

The invention relates to a method of synthesis of aromatic diaminododecane, in particular the production of 3,4'-diamino-4-R-benzophenone of the General formula

where R=Cl, Br, F, CH3The co3,

which were used as intermediates in the synthesis of azo dyes.

A method of obtaining 3,4'-diaminobenzophenone, comprising the following stages: nitration substituted diphenylmethane 94% HNO3(d=1.50) at a temperature of 70-75°C for 12 h and catalytic hydrogenation of dinitropropyl catalyzed by 5% Pd/C, the process is carried out for 7 hours at a temperature 45-47°C. (Process for the preparation of 3,3'- or 3,4'-diaminobenzophenones. Y.Keizaburo, S.Kenichi, T.Yoshimitsu, K.Saburo, Y.Akihiro. Pat. 4618714 USA. Appl. 02.05.83, publ. 21.10.1986. RICH NP, 1987).

The disadvantages of this method of synthesis diaminobenzophenone are: the use of aggressive, harmful chemicals (concentrated HNO3), the use of expensive catalyst (Pd/C), prolonged the time course of each stage of the process, and the need to create the hard conditions of the processes, which inevitably leads to the decrease of the degree of purity and outputs the obtained compounds.

the Purpose of the invention - reducing the cost of synthesis, optimization of reaction conditions - reducing the time and temperature of the process, improving purity and yields of the target products.

This objective is achieved in that the reducing agent is used SnCl2·2H2O, this is no longer a need to use expensive catalyst. Besides possible electrochemical regeneration of this reagent. Instead concentrated HNO3is more convenient in the exercise of synthesis KNO3manufactured by industrial methods.

Nitration of substituted substrates is carried out for 5 hours at a temperature of 20°and a molar ratio of 4'-nitro-4-R-benzophenone:KNO3=1.0:1.15 (prototype 70-75°s, 12 h), the substitution of the halogen is carried out in DMF medium in the presence of K2CO3at a temperature of 40-60°and a molar ratio of substrate:nucleophile=1.0:1.05, recovery of 3,4'-dinitro-4-R-benzophenone carried out with a solution of SnCl2·2H2O 18%hydrochloric acid and the molar ratio of 3,4'-dinitro-4-R-benzophenone:SnCl·H2O=1:6 at a temperature of 20°within 0,15 h, which allows to reduce the temperature 45-47°to 20°and to reduce the process time from 7 h to 0.15 PM

The structure and purity of intermediates and target 3,4'-diamino-4-R-benzophenone analyzed metoder, the melting point and elemental composition.

The invention is illustrated by the following examples.

Example 1. 3,4'-dinitro-4-chlorobenzophenone

To a solution of 15 g (0.06 mol) of 4'-nitro-4-chlorobenzophenone in 150 ml of concentrated sulfuric acid portions contributed 6.9 g (0,069 mol) KNO3. The reaction was carried out for five hours at a temperature of 20°C. Then the reaction mass was poured into water, the precipitate was filtered, dried and recrystallized from a mixture of propanol-2 and N,N-dimethylformamide (3:1). Get 18 g (97.4% of theory) of 3,4'-dinitro-4-chlorobenzophenone yellow powder, TPL 127-129°C.

Found, %: From 50.7; H 2,5; N 9,2.

Calculated, %: C Of 50.9; H 2,5; N 9,3.

1N PMR (DMSO-d6) δMD: 8.82 (d, 2 H, H3'N5', J=9.5), 8.71 (d, 1 H, H2, J=1.9), 8.18 (m, 3H, H2'N6'N6), 7.87 (d, 1 H, H5, J=8.9).

Similarly receive 3,4'-dinitro-4-R-benzophenone, where R=Br, F, CH3The co3. Physico-chemical characteristics of these structures are given in table 1.

Table 1.
No.RMP., °Output %FoundBrutto-formulaCalculated
NN NN
1Br129-13197.544.32.17.9C13H7BrN2O544.42.07.9
2F110-11397.053.612.549.49C13H7FN2O553.82.49.6
3CH3113-11497.958.63.49.8C14H10N2O558.73.59.7
4Och3168-17197.755.73.29.3C14H10N2O655.63.39.2

Example 2. 3,4'-dinitro-4-(4-chlorphenoxy)benzophenone

To 10.1 g (0.07 mol) of potassium carbonate and 6.9 g (0.05 mol) of 4-chlorophenol in 50 ml of N,N-DMF contributed 15 g (0,048 mol) of 3,4'-dinitro-4-chlorobenzophenone. The reaction was conducted for 5 hours at a temperature of 40-60°C. Then the reaction mixture was poured into water, the precipitate was filtered and recrystallized from a mixture of propanol-2 and N,N-dimethylformamide (3:1). Get 19 grams (97% of from theory) of 3,4'-dinitro-4-(4-chlorphenoxy)benzophenone - yellow powder, TPL 142-144°C.

Found, %: 57,1; N 2,89; N 7,1.

Calculated, %: 57,2; N 2,7; N 7,0.

1N PMR (DMSO-d6) δMD: 8.41 (d, 2 H, H3'N5', J=10.4), 8.38 (d, 1 H, H2, J=1.8), 8.09 (d.d., 1H, H6, J=8.8, J=1.5), 8.02 (d, 2 H, H2'N6', J=9.6), 7.58 (d, 2H, H(3)N(5), J=9.1), 7.31 (d, 1H, H5, J=8.7), 7.24 (d, 2H, H(2)H(6), J=9.4).

Similarly receive 3,4'-dinitro-4-R-benzophenone, where R=

,,,.

Physico-chemical characteristics of these structures are shown in table 2.

Table 2.
No.RMP., °Output %FoundBrutto-formulaCalculated
NNCNN
1114-11697.057.24.111.6C17H15N3O657.14.211.7
2192-194 96.962.73.611.5C19H13N3O562.83.611.5
3176-17797.163.83.811.2C20H15N3O563.64.011.1
4150-15297.558.24.615.2C18H18N4O558.34.815.1

Example 3. 3,4'-diamino-4-chlorobenzophenone

To a solution of 5 g (0.016 mol) of 3,4'-dinitro-4-chlorobenzophenone in 20 ml of isopropyl alcohol at a temperature of 40°prilisaetsa solution 43.39 g (0.192 mol) of tin chloride (SnCl2·2H2O) in 20 ml of 18% HCl. Through 0.15 h, the reaction mixture podslushivaet 25% ammonia solution to pH=8 and extracted with several portions of chloroform (S=400 ml). After distillation of the chloroform obtain 3.6 g (95.1% of theory) of 3,4'-diamino-4-chlorobenzophenone yellow powder, TPL 159-160°C.

Found, %: With 63.4; H 4,2; N 11,1.

Calculated, %: C 63,2; N. Of 4.4; N, 11.3.

1N PMR (DMSO-d6) δMD: 7.53 (d, 2H, H2'N6', J=10.0), 7.45 (d, 1H, H5, J=9.51), 7.05 (d, 1H, H2, J=1.6), .67 (d.d., 1H, H6, J=8.7, J=1.4), 6.60 (d, 2H, H3'N5', J=9.0), 6.15 (s, 2H, NH2), 5.55 (s, 2H, NH2).

Similarly receive 3,4'-diamino-4-R-benzophenone,

where R=Br, F, CH3The co3,

,,,.

Physico-chemical characteristics of these structures are shown in tables 3 and 4.

74.2
Table 3.
No.RMP., °Output %FoundBrutto-formulaCalculated
NNCNN
1Br160-16194.753.43.99.5C13H11BrN2O53.63.89.6
2F107-10994.367.54.912.2C13H11FN2O67.84.812.1
3CH3177-17895.16.412.2C14H14N2O74.36.212.3
4Och3154-15594.969.55.611.3C14H14N2O269.45.811.5
5227-22894.568.46.314.2C17H19N3O268.66.414.1
6255-25694.675.05.513.6C19H17N3O75.25.613.8
781-8294.775.76.213.1C20H19N3O75.66.013.2
8212-21395.369.47.317.9C18H22N4O69.67.118.0
9188-18994.967.24.68.1C19H15N2O2Cl67.34.48.2

tr>
Table 4.
No.R1N PMR (DMSO-d6) δMD:
1Br7.53 (d, 2H, H2'N6', J=10.0), 7.45 (d, 1H, H5, J=9.51), 7.05 (d, 1H, H2, J=1.6), 6.67 (d.d., 1H, H6, J=8.7, 1.4), 6.60 (d, 2H, H3'N5', J=9.0), 6.15 (s, 2H, NH2), 5.55 (s, 2H, NH2).
2F7.51 (d, 2H, H2'N6', J=8.0), 7.10 (d, 1H, H5, J=9.55), 7.06 (s, 1H, H2), 6.75 (m, 1H, H6), 6.60 (d, 2H, H3'N5', J=7.0), 6.70 (s, 2H, NH2), 5.35 (s, 2H, NH2).
3CH37.50 (d, 2H, H2'N6', J=10.0), 6.95 (d, 1H, H5, J=7.55), 6.85 (s, 1H, H2), 6.75 (d, 1H, H6, J=7.5), 6.60 (d, 2H, H3'N5', J=9.0), 5.55 (s, 2H, NH2), 4.55 (s, 2H, NH2), 2.15 (s, 3H, CH3).
4Och37.50 (d, 2H, H2'N6', J=10.0), 7.02 (s, 1H, H2), 6.85 (m, 2H, H5N6), 6.58 (d, 2H, H3'N5', J=9.0), 5.99 (s, 2H, NH2), 4.80 (s, 2H, NH2), 3.84 (s, 3H, och3).
57.55 (d, 2H, H2'H6', J=10.0), 7.05 (d, 1H, H2, J=1.0), 6.8-6.9 (m, 2H, H5N6), 6.55 (d, 2H, H3'N5', J=9.5), 5.55 (s, 2H, NH2), 4.65 (s, 2H, NH2), 3.8 (m, 4H, N(CH2)2), 2.9 (m, 4H, O(CH2)2).
67.50 (d, N2'N6', J=8.9), 7.32 (s, 1H, NH), 7.15 (d, 1H, H2, 1.0), 7.06 (t, 2H, H(3),H(5), J=10.0), 6.89 (d.d., 1H. N6, J=7.0, 1.2), 6.80 (d, 2H, H3'N5', J=10.0), 6.65 (d, 1H, H5, J=7.75), 5.58 (t, 1H, H(4), J=10.0), 7.4 (d, 2H, H(2)N(6), J=9.5), 6.02 (s, 2H, NH2), 4.98 (s, 2H, NH2).
77.52 (d, 2H, H2'H6', J=9.5), 7.29 (s, 1H, NH), 7.07-7.13 (m, 3H, H2N6N(5)), 6.87 (d.d., 1H, H(6), J=9.5, 1.5), 6.80 (m, 2H, H(2)N(4)), 6.64 (d, 1H, H5, J=9.0), 6.60 (d, 2 H, H3'N5', J=10.0), 5.99 (s, 2H, NH2), 4.99 (s, 2H, NH2), 2.25 (s, 3H, CH3).
87.49 (d, 2H, H2'N6', J=10.0), 7.02 (d, 1H, H2, J=1.5), 6.94 (d, 1H, H5, J=9.0), 6.85 (d.d., 1H, H6, J=10.0, 1.5), 6.58 (d, 2H, H3'N5', J=9.5), 6.00 (s, 2H, NH2), 4.85 (s, 2H, NH2), 2.85 (s, 2CH2N(2)N(6)), 2.55 (s, 2CH2N(3)N(5)), 2.23 (s, CH3).
9 7.55 (d, 2 H, H2'N6', J=9.5), 7.42 (d, 2 H, H(3)N(5), J=9.7), 7.12 (d, 1 H, H2, J=1.5), 7.03 (d, 2 H, H3'N5', J=9.0), 6.86 (d, 1 H, H5, J=9.1), 6.81 (d.d., 1-N, N6, J=8.9, 1.9), 6.62 (d, 2 H, H(2)N(6), J=9.5), 6.09 (s, 2H, NH2), 5.24 (s, 2H, NH2).

Example 4. Receiving azo dyes based on 3,4'-diamino-4-R-benzophenone,

where R=Br, F, CH3The co3,

,,,.

These diamines diasterous under standard conditions by the action of sodium nitrite in the environment of hydrochloric and sulfuric acids. Received diazocompounds proved himself as an active datastudio in the azocoupling reaction with aromatic hydrocodoneee benzene, naphthalene and heterocyclic series. On the basis of the synthesized bestcradite having high resistance to dry and wet rubbing, washing and perspiration, the General formula:

where R1=,,,

The method of obtaining 3,4'-diamino-4-R-benzophenone of the General formula

3The co3,

including nitration of substituted 4'-nitro-4-R-benzophenone potassium nitrate in sulfuric acid, nucleophilic substitution of the halogen (for R=Cl) in collaboration with O - and N-nucleophiles and recovery of 3,4'-dinitro-4-R-benzophenone of the General formula

where R=Cl, Br, F, CH3The co3,

chloride tin (II) in acidic water-ethanol solution, characterized in that the nitration of substituted substrates is carried out for 5 hours at a temperature of 20°and a molar ratio of 4'-nitro-4-R-benzophenone:KNO3=1,0:1,15, substitution of the halogen is carried out in DMF medium in the presence of K2CO3at a temperature of 40-60°and a molar ratio of substrate:nucleophile=1,0:1,05, recovery of 3,4'-dinitro-4-R-benzophenone carried out with a solution of SnCl2·H2O 18%hydrochloric acid and the molar ratio of 3,4'-dinitro-4-R-benzophenone:SnCl2·2H2O=l:6 at a temperature of 20°within 0,15 o'clock



 

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3 cl, 3 dwg, 4 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,

that are used as intermediate product in synthesis of azo dyes useful for staining protein fibers and possessing the unique indices of thermal stability. Method involves steps for nitration reaction of substituted benzophenones with potassium nitrate in concentrated H2SO4, nucleophilic replacing halogen (wherein R means Cl) in interaction with O- and N-nucleophilic compounds in dimethylsulfoxide (DMSO) medium in the presence of K2CO3 and reduction of 3,4'-dinitro-4-R-benzophenones. The nitration reaction of synthesized benzophenones is carried out at temperature 20oC for 5 h in the mole ratio 4'-nitro-4-R-benzophenone : KNO3 = 1.0:1.15. Nucleophilic replacing halogen is carried out at temperature 40-60oC for 1-5 h in the mole ratio substrate : nucleophilic compound = 1.0:1.05, and reduction of dinitrobenzophenones is carried out with SnCl2 x 2H2O in 18% HCl medium, in the mole ratio 3,4'-dinitro-4-R-benzophenone : SnCl2 x 2H2O = 1:6, at temperature 20oC for 0.15 h. Invention provides decreasing cost of synthesis, reducing time and temperature in carrying out the process, enhancing purity and yield of end products.

EFFECT: improved method of synthesis.

4 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of continuous production of alkylamino(meth)acrylamide of formula (C) by reacting a formula (B) compound with a formula (A) compound in the presence of a re-esterification catalyst in the presence of at least one polymerisation inhibitor in a continuous re-esterification installation. Reacting substances are continuously fed into the corresponding reactor (1) and the alcohol formed from the reaction is continuously removed in form of an azeotropic mixture of methanol and methyl(meth)acrylate (13) (mixture of ethanol and ethylacrylate 13, respectively) using a distillation column (2). The reaction mixture is constantly fed from the reactor into the distillation column (3) or, respectively, into evaporator (5). Highly volatile components (A, B, methanol or, respectively, ethanol) and a very small part of amide end product (C) are tapped from the head of the column and returned to the reactor. Amide end products (C) together with catalyst and polymerisation inhibitor, as well as heavy by-products are tapped from the bottom of the column. Material flow (15) from the bottom of the distillation column (3) is continuously taken for distillation to obtain pure end product.

EFFECT: improved quality of product, high efficiency and output.

15 cl, 1 tbl, 1 ex, 1 dwg

FIELD: chemistry.

SUBSTANCE: improved method of producing 2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one dihydrochloride, known as thylorone or amixine, and used as an immunostimulating and antiviral agent, involves treating 2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one in methylene chloride with hydrogen chloride in gaseous state of in form of hydrochloric acid, preferably in molar ratio 2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one : hydrochloric acid equal to 1:2.05-3.0. A solution of 2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one dihydrochloride in methylene chloride is obtained, which is cooled to temperature not below minus 12C to obtain a suspension and then filtered and dried. The filtered residue is dried in inert gas or air at temperature from 90 to 110C or in a vacuum, as a rule. Completion of salt formation is usually controlled from increase in temperature of the reaction mass and its stabilisation to a value between 32 and 34C, as well as from the pH value, which must not be higher than 4.0. The filtered residue is dried in an inert gas or air, at temperature from 90 to 110C or in a vacuum, as a rule.

EFFECT: simplification of the process due to exclusion of inflammable solvents and obtaining a product of high quality with high output.

6 cl, 1 dwg, 3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing and aminophenol compound of formula (1) , where each of R1 and R2, which can be identical or different, are a hydrogen atom, C1-C6 alkyl group, which can be substituted with phenyl, or phenyl; R1 and R2 together with the neighbouring nitrogen atom can form a 5- or 6-member heterocyclic group, selected from piperidinyl and piperazinyl; the heterocyclic group can be substituted with one substitute selected from hydroxyl group, C1-C6 alkyl group and phenoxy group, which can have a C1-C6 alkoxy group, substituted with 1-3 halogen atoms. The method involves reacting a cyclohexanedione compound of formula (2) with a amine compound of formula (3) , where R1 and R2 assume values given above, in neutral or basic conditions.

EFFECT: wider range of use of the compound.

8 cl, 4 dwg, 13 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method for synthesis of 4-(dimethylamino)-1-alkyl-1-methyl-2-alkyn-1-ols of general formula (1): where R=C2H5, C4H9, C6H13, which are substances with physiological activity, particularly cholinolytic properties. The method involves reacting 3-alkyl-3-methyl-1-alkyn-3-ols with N,N,N1,N1-tetramethylmethanediamine in the presence of a copper monochloride catalyst in molar ratio 3-alkyl-3-methyl-1-alkyn-3-ol: N,N,N1,N1-tetramethylmethanediamine: CuCl=10:(10-12):(0.4-0.6) in an argon atmosphere at temperature 50-90C and atmospheric pressure, predominantly at 80C, for 3-5 hours. Output of 4-(dimethylamino)-1-alkyl-1-methyl-2-alkyn-1-ols (1) is 84-96%.

EFFECT: method increases output of products.

1 cl, 3 dwg, 1 tbl, 12 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing 2-[(dimethylamino)methyl]phenol used in the food industry and medicine, as well as lubrication and engine oil additives, corrosion inhibitors for different types of steel, stabilisers of motor car and rocket fuel, monomers, plastic and different types of rubbers. The method involves reacting phenol with N,N,N,N-tetramethylmethylenediamine. The reaction is carried out in the presence of a copper (I) chloride catalyst in molar ratio phenol: N,N,N,N-tetramethylmethylenediamine: CuCl=10:(10-11):(0.2-0.4) at atmospheric pressure, mainly at temperature of 50C for 3.5-4.5 hours.

EFFECT: increased selectivity of the process and output of the desired product, reduced reaction temperature.

1 cl, 2 dwg, 1 tbl, 1 ex

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