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Method for preparing 4-thioureidoiminimethyl-pyridinium perchlorate possessing tuberculostatic activity

Method for preparing 4-thioureidoiminimethyl-pyridinium perchlorate possessing tuberculostatic activity
IPC classes for russian patent Method for preparing 4-thioureidoiminimethyl-pyridinium perchlorate possessing tuberculostatic activity (RU 2265014):
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FIELD: organic chemistry, chemical technology, medicine, phthisiology.

SUBSTANCE: 4-thioureidoiminomethyl-pyridinium perchlorate is prepared from 4-pyridine aldehyde and thiosemicarbazide in the presence of 48-55% perchloric acid for a single stage. The parent reagents - 4-pyridine aldehyde : thiosemicarbazide are taken in the ratio = 1.3:1.0, reaction period is 3-4 h, and reaction temperature is maintained in the range 80-85°C. Invention provides increasing yield and purity of the end product, simplifying technology and reducing cost in its preparing.

EFFECT: improved preparing method.

7 cl, 8 ex

 

The method of producing perchlorate 4-theoreticoinformation-pyridinium, with tuberculostatic activity

The invention relates to improvements in the method of producing perchlorate 4-theorieorientierte high tuberculostatic activity.

Previously the authors of the present invention was patented above-mentioned drug and shows one of the methods of its production (Patent RF №1621449) by the reaction of thiosemicarbazone-4-pyridinylmethyl with perchloric acid. But thiosemicarbazone-4-pyridinediamine (3) was originally obtained by reaction of 4-pyridinediamine (1) thiosemicarbazide (2) in water-ethanol solution at 60-65°C. the Yield of the compound (3) was 74%.

The synthesis of the target product perchlorate 4-theorieorientierte (4) has been received, as indicated above, thiosemicarbazone-4-pyridinediamine (3) and 58%HClO4when heated (80-90° (C) opening 96% (calculated on thiosemicarbazone (3)).

Thus, if we consider the yield of the target product (4) the original thiosemicarbazide (2), it is relatively low at approximately 72%. Moreover, according to the previously proposed method, the need arose for the isolation and purification of intermediate thiosemicarbazone-4-pyridinylmethyl is (3), that was complicated, and therefore made the process more expensive.

The aim of the present invention is to develop a new simple, one-step and more efficient method of producing perchlorate 4-theorieorientierte (4) of the more affordable 4-pyridinediamine (1), seeking thereby reduce the cost and simplify the process technology, to increase the yield and purity of the target product.

This goal is achieved by the synthesis of the target product (4) from 4-pyridinediamine (1), which are taken in excess, thiosemicarbazide (2) and 48-55%perchloric acid in one stage, without prior isolation of intermediate thiosemicarbazone-4-pyridinediamine (3), in water-ethanol solution at 80-85°C. the Yield of the target product when it reaches 96% in the calculation of the original thiosemicarbazide (2).

The invention consists in that the formation of the target product (4) is carried out in one stage in acidic conditions. Perchloric acid, in this case, is not only a supplier of protons and anions ClO4-but is the catalyst for the dehydration of intermediate (A) in the formation of the intermediate thiosemicarbazone 4-pyridinediamine (3).

Stage dehydration of intermediate (A) is catalyzed by perchloric acid at low pH values becomes the table is to fast, what is the limiting factor of the reaction becomes nucleophilic attack of the amine, in this case thiosemicarbazide on the carbonyl group of the aldehyde, thus achieving high output connections (3), and hence the target product (4) [1].

The invention is illustrated by the following examples:

Example 1. Perchlorate 4-theorieorientierte (4).

To 1500 ml of distilled water is added 91 g (1 mol) of thiosemicarbazide (2), heated to 70°and intensively stirred at this temperature for 50 minutes until complete dissolution of thiosemicarbazide (2). To the resulting solution at 70°slowly added a solution of 200 ml of 48-55%perchloric acid in 200 ml of distilled water and then the solution 117,7 (1,1 mol) (104,2 ml) of fresh 4-pyridinediamine (1) in 200 ml of ethanol and 1300 ml of distilled water. Adding 1/3 volume solution of 4-pyridinediamine (1) when mixing is observed loss of a yellow crystalline precipitate. The reaction mixture is heated to 80-85°add the remaining solution of 4-pyridinylmethyl, stirred at this temperature for 3 hours, cooled to room temperature and allowed to stand for 1 hour. The reaction mixture is cooled to + 3-5°C, the precipitation of the desired product (4) is filtered by the filter SCHOTT, washed with 10 l of ice water, and then 200 ml of holodnogo ethyl alcohol and dried in a vacuum desiccator to constant weight for 40 minutes. Received 268,5 g of compound (4), 96% (based on thiosemicarbazide. Light yellow crystals with TPL 231-234°

IR spectrum, νcm-1: 3440 (NH2), 3320 (NH), 3150 (N+H), 1640 (C=N), 1380 (C=S), 1275 (C-N), 1120 (ClO4-). NMR1N, DMSO-d6that δ, ppm: 8.14 (1H, CH=N); 8.50-8.85 m (6N,5H4N, NH2); 11.41 n. (1H, N+H in the cycle); 12.15 (1H, NH)YR13With, DMSO-d6that δ ppm: 179.2(C=S); 150.5 (CH); 142.3 (C-2,6 cycle); 136.3 (C-4 cycle); 123.7 (C-3,5 cycle). In the UV spectrum of compound (4) in ethanol there is one absorption band at 326 nm.

Found, %: C 30.22; N, 3.30; Cl 12.60; N 20.15; S 11.48. With7H9ClNO4S.

Calculated, %: 29.95; N, 3.23; Cl 12.63; N 19.96; S 11.42.

Example 2. The influence of the ratio of the reactants.

In reaction take 91 g (1 mol) of thiosemicarbazide (2), 107 g (1 mol) of 4-pyridinediamine (1) and 200 ml of 48-55%HClO4(equimole number). Conduct the reaction and process the target product (4)as in example 1. Output connections (4) 209.8 g (75%). TPL 231-233°C.

Example 3. The influence of the reaction temperature.

In reaction take 91 g (1 mol) of thiosemicarbazide (2), 117.7 g (1.1 mol) of 4-pyridinylmethyl, 200 ml of 48-55%HClO4conduct the reaction at 50-55°and process the target product (4)as in example 1. Output connections (4) 134,1 g (48%). TPL 230-233°C.

Example 4. The influence of the reaction temperature.

In reaction take 91 g (1 mol) of thiosemicarbazide (2), 117.7 g (1.1 mol) of 4-pyridi the aldehyde (1), 200 ml of 48-55%HClO4conduct the reaction at 65-70°and process the reaction product as in example 1. Output connections (4) 201,4 g (72%). TPL 231-233°C.

Example 5. The influence of the reaction temperature.

In reaction take 91 g (1 mol) of thiosemicarbazide (2), 117.7 g (1.1 mol) of 4-pyridinediamine (1), 200 ml of 48-55%HClO4conduct the reaction at 95-110°and process the reaction product as in example 1. At this high temperature there is a significant resinification of the reaction mixture and the yield of the target product (4) is 134,3 g (48%). TPL 231-234°C.

Example 6. The effect of the order of addition of reagents.

In the reaction flask 1500 ml of distilled water, 200 ml of ethanol and simultaneously added 91 g (1 mol) of thiosemicarbazide (2), 200 ml of 48-55%HClO4and 117.7 g (1.1 mol) of 4-pyridinediamine (1). Conduct the reaction and process the reaction product as in example 1. Output connections (4) 162.2 g (58%, based on thiosemicarbazide). TPL 231-234°C.

Example 7. The influence of the duration of the reaction.

The reaction is carried out with the same quantities of reagents as in example 1, but reduce the total reaction time of 5 hours 30 minutes to 3 hours. Conduct the reaction process and the product of reaction (4), as in example 1. Output 89.4 g (32%). TPL 231-234°C.

Example 8. The effect of excess perchloric acid.

In reaction take 91 g (1 mol) of thiosemicarbazide (2), 117.7 g (1.1 mol) of pyridinoline (1) and excess (350 ml) 48-55%HClO 4. Conduct the reaction process and the target reaction product as in example 1. Target product (4) is washed on the filter from SCHOTT perchloric acid with 16 liters of distilled water. Output connections (4) 218.2 g (78%). TPL 229-232°C.

Sources of information

1. General organic chemistry. - M.: Publishing house "Chemistry", 1982. - Volume 2. - S.

1. The method of producing perchlorate 4-theorieorientierte formula

with tuberculostatic activity, characterized in that the target product is obtained from 4-pyridinylmethyl and thiosemicarbazide in the presence of 48-55%perchloric acid in one stage.

2. The method according to claim 1, characterized in that the starting reagents-4-pyridinylmethyl: thiosemicarbazide take in a weight ratio of 1.3:1.0 in.

3. The method according to claim 1, characterized in that the sequence of introduction of the reagents in the reaction is performed in the order: water solution thiosemicarbazide add an aqueous solution of chloric acid and then an aqueous-ethanolic solution of 4-pyridinylmethyl.

4. The method according to claim 1, characterized in that the reaction time is 3-4 hours

5. The method according to claim 1, characterized in that the volume ratio of water: ethanol is 15:1.

6. The method according to claim 1, characterized in that the reaction temperature is maintained in the range of 80-85°C.

7. The method according to claim 1, characterized in that DL the reactions take perchloric acid in relation to 4-pyridinylmethyl in a volume ratio of 1.9:1.0 in.

 

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