Production method for methyl ethers of 2-thiophen carbonic acid and its derivatives

FIELD: chemistry.

SUBSTANCE: invention is related to the field of organic chemistry, in particular, to method for production of methyl ethers of 2-thiophen carbonic acid intended for use in synthesis of optical whiteners, dyes for cotton, wool, artificial fibers, medical preparations, and also as additive to oils or hydraulic liquids. Substance of the method consists in thiophen interaction with methanol in presence of carbon tetrachloride under action of catalysts - oxo-bis-(2,4-pentanodionato)vanadium VO(acac)2 or tris (2,4-pentanodionato)iron Fe(acac)3, or molybdenum hexacarbonyl Mo(CO)6 at the temperature of 130-170°C for 3-6 hours at the following mole ratio - catalyst:thiophen:CCl4:methanol equal to 1:100:200-300:200-300.

EFFECT: suggested method makes it possible to produce target product with yield of 63-85%, using simplified technology.

1 tbl, 14 ex

 

The present invention relates to the field of organic chemistry, in particular to a process for the preparation of esters of 2-thiophencarboxylic acid.

2-Thiophenecarbonitrile acids and their derivatives find application in the synthesis of optical brighteners, dyes for cotton, wool, synthetic fibres and the like, drugs, and also used as additives to oils or hydraulic fluids (Lienency, Appahare, Maalik, Vpityu, Pimstone, Sestic, Bpharmacy. New directions in the chemistry of thiophene. M., Nauka, 1976, 424 S. [1]).

Methyl ether thiophencarboxylic acid (TFA) usually get chlorotoluene derivatives of thiophene, the hydrolysis of 2-chloromethylstyrene, subsequent oxidation of the resulting alcohol with nitric acid and esterification with methanol (T.Sone, Y.Abe, T.Oikawa. J. Chem. Soc. Jap. Pure Chem. Sec., vol.92, No. 12, 1193-1198, A68(1971) [2]).

In chemical resistant glass at 0°C is placed 5 moles of thiophene and 200 ml of concentrated hydrochloric acid with vigorous stirring the mixture continuously transmit the rapid current of hydrogen chloride, when the temperature reaches 0°C, to the contents of the beaker are added 500 ml of a 37%solution of formaldehyde such a rate that the temperature remained below 5°C. This operation takes ~4 hours. After appropriate processing of the reaction mixture (ek the traction ether, washing of the extracts with saturated solution of Na2CO3the drying anhydrous CaCl2, removing the solvent and distillation under vacuum) output 2-chloromethylstyrene is 40%.

Then 1.3 g of 2-chloromethylstyrene and 25 ml of HNO3(d 1.38) is heated for 90 min at 60-70°C, evaporated to dryness on a water bath, the residue is dissolved in 15 ml of dilute NaOH, oxidize (5 hours, 20°C) 60 ml of 3%aqueous KMnO4and get 2-thiencarbazone acid with a yield of 85%. Subsequent esterification of 2-thiophencarboxylic acid get its methyl ester.

The method has some significant drawbacks:

1. A multi-stage process.

2. Significant losses during the stepwise selection of intermediate products.

3. Using a strong acid (HNO3H2SO4), which requires neutralization of the reaction mixture after completion of the process.

4. The complexity of the selection of the target product due to the formation of by-products and a significant amount of waste and wastewater that must be disposed.

Butyl ether 2-thiophencarboxylic acid can be obtained by disproportionation and isomerization of acetals of 2-formylthiophene on the surface of Al2About3and Al2(SO4)3at 200°C (S.Raja, N.Xavier, S.J.Arulraj. Indian J. Chem., Sect. Century, 27B. No. 10, 916-919(1988) [3]).

Disadvantages of the method:

1. The inaccessibility of the outcome of the s acetals.

2. The high reaction temperature (200°C).

3. The complexity in the process of allocating butyl ether 2-thiophencarboxylic acid due to the formation of by-products (aldehyde, a simple ether).

Isomerization and rearrangement of 2-thiopheneacetic catalyze apirat boron TRIFLUORIDE [(C2H5)2OBF3], or chloride of tin. The reaction takes place in an environment dichloroethane (S.Raja, N.Xavier, S.J.Arulraj. Indian J. Chem., Sect. In, 28V, No. 8, 687-689(1989) [4]).

A solution of acetal (0,1 mol) of purified 1,2-dichloroethane (50 ml) cooled to 0°C and add fresh catalyst (0,1 mol) in a solution of 1,2-dichloroethane (50 ml) drip for 15 min in anhydrous conditions, the reaction mixture was incubated for another 15 min, add cold water, washed with a mixture of 5% aqueous solution of Na2CO3and with water to a neutral environment, dried Na2SO44 hours.

Disadvantages of the method:

1. The inaccessibility of the initial reagents.

2. The use of stoichiometric amounts of catalyst (1:1).

3. Conducting the reaction at 0°C.

4. 1,2-Dichloroethane refers to highly toxic substances.

5. Neselektivno process that creates difficulties in the selection of the target product.

The esters of 2-thiophencarboxylic acid (TFA) is obtained by esterification using 2-4 equivalent BF3·Et2O and excess alcohol ROH (R=C1-4and the keel and cyclohexyl) boiling the mixture for 1.25-48 h (Kadaba, Pankaja K.Synthesis, No. 11, 628-630(1972) [5]).

Methyl esters of 2-thiophencarboxylic acid, mixed with in the fifth position, receive at their boiling in methanol in the presence of N2SO4for 4-4 .5 hours (H.Satonaka. Bull. Chem. Soc. Jpn., v.56, 2463-2468(1983) [6]).

Methyl ester 2-thiophencarboxylic acid derived from 2 - thio-fingerbones acid via the acid chloride sequential processing of its excess thionyl chloride and then with methanol in the presence of pyridine (R.Nato, G.Consiglio, A.Storace. J. Chem. Soc. Perkin Trans II, No. 15, 1805-1808(1976) [7]).

The disadvantages of the methods:

1. Inaccessibility thiophenecarboxylic acids.

2. Using as catalyst a strong inorganic acid (H2SO4), Lewis acids (BF3·Et2About) and gloriously agents (SOCl2), which requires disinfection after completion of the reaction and disposal of waste and sewage.

The esterification of TPA was carried out using an excess of diazomethane CH2N2in dry ether (R.Ugo, A.Chiesa, P.Nardi, R.Psaro. J.Mol. Catal. V.59, No. 1, 23-31(1990) [8]).

To obtain the ethyl ester of 2-thiophencarboxylic acid mixture of thiophene, carbon tetrachloride (CCl4) and potassium hydroxide (KOH) was heated for 4 hours in ethanol at 150°C in an autoclave. After neutralizes and and distillation in vacuum with the release of 23% was obtained ethyl ester 2-thiophencarboxylic acid (K.L.Kreuz. Thiophene carboxylic acids. U.S. 2,552,978 (1951) [9]).

On the basis of similarity according to three criteria (source reagents - thiophene, alcohol CCl4education in the reaction of ester 2-thiophencarboxylic acid) the prototype was taken method for the synthesis of esters of 2-thiophencarboxylic acid from thiophene and alcohol [9].

The prototype has the following disadvantages:

1. The low yield of the desired product (23%).

2. The use of large amounts of alkali (KOH)to neutralize it after completion of the reaction.

3. The formation of large quantities of inorganic waste (KCl) and wastewater that must be disposed.

In this regard, the authors were tasked to obtain methyl esters of 2-thiophencarboxylic acid with higher outputs, to simplify and reduce the cost of technology.

The method consists in the interaction of thiophene with methanol in the presence of carbon tetrachloride under the action of catalysts-oxo-bis-(2,4-pentanedionato)vanadium VO(ASAS)2[or Tris(2,4-pentanedionato)iron Fe(ASAS)3or hexacarbonyl molybdenum Mo(CO)6] at a temperature of 130-170°C for 3-6 h at a molar ratio of [VO(acac)2or Fe(ASAS)3or Mo(CO)6]: [thiophene]:[CCl4]:[methanol]=1:100:200÷300:200÷300.

Under optimal conditions, the yield of methyl esters of 2-thio is inkarbaeva acid reaches 63-85% depending on the nature and position of Deputy. In the absence of CCl4the reaction does not go.

Significant differences of the proposed method from the prototype.

1. To obtain the methyl ester of 2-thiophencarboxylic acid from thiophene use systems CCl4-CH3HE-Mo(CO)6, CCl4-CH3HE-Fe(ASAS)3, CCl4-CH3HE-VO(ASAS)2generating in situ a strong oxidant methylhippuric.

The advantages of the proposed method.

1. The lack of aggressive oxidants.

2. The high yield of the target products.

3. The selectivity of the process.

4. The availability and low cost catalysts.

5. Reduce the cost and simplify the technology as a whole by reducing energy and labor costs.

The proposed method is illustrated by examples:

EXAMPLE 1. The reaction is carried out in a glass ampoule (V=20 ml) or mikroavtobus stainless steel (V=17 ml).

In mikroavtobus (ml) under argon was placed 0.1 mmol of Mo(CO)6

[or Fe(ASAS)3, VO(ASAS)2], 10 mmol of thiophene or its derivative), 20-30 mmol CCl4and 20-30 mmol of CH3HE, autoclave, sealed (the ampoule was sealed and heated at 140-170°C for 3-6 hours with constant stirring. After the reaction, the autoclave (ml) is cooled to 20°C., opened, the reaction mass is filtered through a layer of silica gel (2 g) (eluent - hexa is: ether = 1:1). The solvent is distilled off, the residue is distilled in vacuum.

Dedicated methyl esters of 2-thiophenecarbonitrile acids have the following constants:

Methyl ester 2-thiophencarboxylic acid: TKIP-121°C/10 PA. An NMR spectrum13With (CDCl3, δ, ppm, TMS): 133.75 (C-2), 133.42 (C-3), 127.11 (C-4), 131.86 (C-5), 161.64 (C=O), 51.22 (och3). Mass spectrum, m/z (J. (%)): 142 [M]+(35), 38 (12), 39 (45), 45 (7), 57 (9), 81 (5), 82 (7), 83 (12), 110 (39), 111 (100), 112 (10), 113 (7), 141 (24). Found (%): 57.05; H 4.72; S at 25.45. With6H6O2S. Calculated (%): 57.11; H 4.79; S 25.41; O 12.69. Yield 85%.

Methyl ester 5-methyl-2-thiophencarboxylic acid: TKIP-96°C/10 PA. An NMR spectrum13With (CDCl3Oh , ppm, TMS): 131.36 (C-2), 133.90 (C-3), 125.94 (C-4), 147.43 (C-5), 161.95 (C=O), 51.18 (och3), 14.87 (CH3). Mass spectrum, m/z (J. (%)): 156 [M]+(40), 39 (5), 45 (12), 57 (24), 69 (5), 97 (10), 125 (100), 126 (12), 127 (5), 155 (5). Found (%): 53.79; H 5.11; S 20.57. C7H8O2S. Calculated (%): 53.82; N, 5.16; S 20.52; 20.50. Yield 78%.

Methyl ester 5-ethyl-2-thiophenecarboxylic acid: TKIP-120°C/10 PA. An NMR spectrum13With (CDCl3, δ, ppm, TMS): 131.16 (C-2), 133.84 (C-3), 126.13 (C-4), 147.20 (C-5), 161.90 (C=O), 51.13 (och3), 29.95 (CH3), 15.64 (CH3). Mass spectrum, m/z (J. (%)): 170 [M]+(60), 39 (17), 41 (7), 45 (17), 51 (7), 53 (6), 57 (5), 58 (4). 59 (5), 65 (10), 66 (5), 67 (9), 69 (10), 70 (8), 71 (6), 77 (10), 78 (7), 95 (5), 96 (10), 97 (6), 111 (17), 124 (10), 127 (12), 139 (71), 154 (7), 155 (100). 156 (8), 169 (7). Found (%): 56.35; H 5.89; S 18.85. C8H10O2S. Calculated (%): at 56.44; H 5.92; S 18.35; 9.29. Yield 65%.

Methyl ester of 5-acetyl-2-thiophencarboxylic acid: TKIP-128°C/1 PA. An NMR spectrum13C (CDCl3, δ, ppm, TMS): 139.36 (C-2), 133.40 (C-3), 131.58 (C-4), 148.43 (C-5), 161.95 (C=O), 52.18 (och3), 19.50 (C=O), at 26.87 (CH3). Mass spectrum, m/z (J. (%)): 184 [M]+(32), 39 (33), 43 (17), 45 (9), 57 (7), 58 (6), 83 (17), 110 (5), 111 (100), 112 (7), 124 (10), 127 (14), 154 (8), 169 (7), 170 (12), 171 (6), 183 (5). Found (%): 52.11; N, 4.29; S 17.42. C8H8O3S. Calculated (%): at 52.16; H 4.38; S 17.41; 26.05. Yield 85%.

Methyl ester of 5-chloro-2-thiophencarboxylic acid: TKIP-88°C/5 PA. An NMR spectrum13With (CDCl3, δ, ppm, TMS): 132.01 (C-2), 133.13 (C-3), 127.17 (C-4), 137.64 (C-5), 161.46 (C=O), 52.21 (och3). Mass spectrum, m/z (J. (%)): 176 [M]+(43), 37 (5), 38 (7), 45 (5), 53 (5), 57 (7), 59 (4), 69 (4), 73 (24), 75 (7), 81 (7), 82 (9), 117 (12), 118 (5), 119 (7), 144 (5), 145 (100), 146 (12), 147 (41), 175 (5). Found (%): 40.73; N, 2.81; C1 19.98; S 18.09. C8H8ClO2S. Calculated (%): 40.80; N, 2.85; Cl 20.07; S 18.15; 0 18.13. Yield 65%.

Methyl ester of 5-bromo-2-thiophencarboxylic acid: TPL 46-47°C. an NMR Spectrum13With (CDCl3, δ, ppm, TMS): 134.64 (C-2), 133.61 (C-3), 130.94 (C-4), 120.17 (C-5), 161.46 (C=O), 52.21 (och3). Mass spectrum, m/z (J. (%)): 221 [M]+(12), 37 (10), 38 (17), 45 (10), 53 (4), 57 (10), 59 (5), 69 (5), 76 (14), 77 (3), 117 (10), 119 (9), 141 (4), 161 (10), 163 (10), 188 (10), 189 (98), 190 (19), 191 (1000), 192 (10), 193 (7), 219 (10), 220 (45). Found (%): at 32.41; H 2.25; Br 36.17; S 14.35. C6H5BrO2S. Calculated (%): 32.59; N, 2.28; Br 36.14; S 14.47; 14.52. Yield 67%.

Other examples of the method shown in the table.

TableThe results of the experiments on the synthesis of the methyl esters of 2-thiophencarboxylic acid using CH3HE CCl4under the action of vanadium, molybdenum and iron-containing catalysts№ № CatalystThe molar ratio of [kat]:[thiophene]: [SN3HE]:[CCl4]Deputy (R) With5Temperature, °CReaction time, hThe yield of methyl esters of 2-thiophencarboxylic acid %12345671.VO(acac)21:100:200:200N1703632.-"--"--"--"-583 3.-"-1:100:300:300-"--"--"-854.-"-1:100:200:200Ac-"--"-855.Fe(ASAS)3-"-N1406656.-"--"-CH3-"--"-787.-"--"-With2H5-"--"-658.-"--"-Cl-"--"-659. -"--"-Br-"--"-6710.Mo(CO)6-"-H13058011.-"--"-CH3-"--"-7512.-"--"-AU-"--"-8213.-"--"-Br-"--"-6314.-"--"-N140-"-84

The way to obtain methyl ester 2-thiophencarboxylic acid and its derivative f is rmula (I)

characterized in that the thiophene is subjected to interaction with methanol in an autoclave under argon in the presence of CCl4under the action of a catalyst selected from the group comprising oxo-bis-(2,4-pentanedionato)vanadium VO(acac)2, Tris(2,4-pentanedionato)iron Fe(ASAS)3and hexacarbonyl molybdenum Mo(CO)6when the molar ratio of catalyst:thiophene:CCl4:methanol = 1:100:200-300:200-300 at a temperature of 130-170°C for 3-6 hours



 

Same patents:

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SUBSTANCE: invention concerns enantiomers of thiophene hydroxami acid derivatives of general formula I and their pharmaceutically acceptable salts. , where Ar is aryl or heteroaryl group selected out of thiophene, morpholine, which can be non-substituted or mono-, di- or trisubstituted by halogen, phenyl, alkyl, -O-alkyl, -OH; R1 is hydrogen, phenyl or alkyl; together with Ar-group R1 forms tetrahydronaphthaline or indane cycle; R2 is hydrogen or alkyl; and their pharmaceutically acceptable salts.

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FIELD: organic chemistry, agriculture, insecticides.

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5 cl, 6 tbl, 27 ex

The invention relates to new derivatives of esters of carboxylic acids of General formula I, where R1represents an alkyl group branched or non-branched chain having 1-4 carbon atoms; R2represents a group of formula IV, in which R4represents a hydrogen atom or etinilnoy group; R5and R6are the same or different selected from the group consisting of a hydrogen atom or a methyl group; R7represents a hydrogen atom; R8selected from propargyl, methoxymethyl or methylthio

The invention relates to a new process for the preparation of esters cyclopropanecarbonyl acid of the formula I

< / BR>
where R is the ester residue, split in neutral or acid medium and which WITH1-18the alkyl possibly substituted with halogen or benzyl radical, possibly substituted on the tops of the aromatic ring by one or more halogen atoms, or a radical of formula (a) -(g),

< / BR>
where R2Is h or methyl;

R3- aryl;

R4- CN, N.;

R5- fluorine, chlorine, bromine or hydrogen;

R6, R7, R8, R9is hydrogen or methyl;

S/1 symbolizes tetrahedrite

The invention relates to a new method of obtaining some of esters of cyclopropane used in the synthesis of important pesticides

The invention relates to new chemical product, particularly, to pentafluorobenzyl 1R, 3S-2,2-dimethyl-3(2-chlorpro - penyl)-cyclopropanecarboxylate formula I

in the form of indivisible mixture of isomers Ia and IB in the ratio from 1: 2 to 1: 4

FIELD: chemistry.

SUBSTANCE: invention is related to the field of organic chemistry, in particular, to method for production of methyl ethers of 2-thiophen carbonic acid intended for use in synthesis of optical whiteners, dyes for cotton, wool, artificial fibers, medical preparations, and also as additive to oils or hydraulic liquids. Substance of the method consists in thiophen interaction with methanol in presence of carbon tetrachloride under action of catalysts - oxo-bis-(2,4-pentanodionato)vanadium VO(acac)2 or tris (2,4-pentanodionato)iron Fe(acac)3, or molybdenum hexacarbonyl Mo(CO)6 at the temperature of 130-170°C for 3-6 hours at the following mole ratio - catalyst:thiophen:CCl4:methanol equal to 1:100:200-300:200-300.

EFFECT: suggested method makes it possible to produce target product with yield of 63-85%, using simplified technology.

1 tbl, 14 ex

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