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The synthesis of 2,6-bis­(phe­nil)­hexahydro-1,3,5-triazine-4-thion

 

Ph.D. A.R.Sujayev

 

Acad. A.M.Guliyev Institute of Chemistry of Additives NASA, Azerbayjan, Beyukshor  str., 2062, AZ 1029, Baku, efsun_07@mail.ru

 

Abstract

By three- component condensation of benzaldehyde, thiourea and 33.5% water solution of ammonia has been synthesized 2,6-bis(phenyl)hexahydro-1,3,5-triazine-4-tion.

Keywords: benzaldehyde, thiourea

 

INTRODUCTION

According to the literature data 2,6-bis­(phenyl)hexahydro-1,3,5-triazine-4-tiones are the class of substances which shows antiseptic, bleaching, explosive and other properties. A lot of their keto derivatives shows physiological activity. For example, 5-aza­siti­din named by 4-amine-1,3,5-triazine-2-on ribofuranozed shows anti- cancer and anti- leukemia features and it is used in medical clinic. In the national industry 6-metyl­amino-1-metyl-3-cyclohexsyl-1,3,5-triazine-2,4-dion or hexazinon used as a herbi­sid in destroying the weeds. 1,3,5-triazine derivatives – melamine, melamineformaldehyde are used in synthesis thermoplastic materials, but cyan chlorine in obtaining the paints. Hexahydro-1,3,5-triazinetions are class of effective antioxidants that have removed the oxidation of model carbohydrogen kumol.

EXPERIMENTAL

The synthesis of 2,6-bis­(phenyl)hexahydro-1,3,5-triazine-4-tion. 11.4 g. (0.15 mol) thiourea, 20 ml isopropyl alcohol and 21.2 gr (0.2 mol) benzaldehyde added to the three – neck flash which equipped with mechanical stirrer, thermometer and drop funnel and dynamically mixed. Then 33.5% water solution of ammonia added slowly to the reaction mixture. Mixed in 4 hours in 25°C temperature. Reaction process have observed with thin - layer chromatography. When the reaction completed the mixture persisted during 24 hours at room temperature and white crystals precipitated. Crystals of 2,6-bis­(phenyl)hexahydro-1,3,5-triazine-4-tion filtrated and separated, then washed in dichloromethane and crystallized in ethyl alcohol. Obtained 7.41 g. of 2,6-bis­(phenyl)hexahydro-1,3,5-triazine-4-tion.

Yield 65%. M. P.= 232°C. Rf=0.54.

Found, %: C 66.91, H 5.67, N 15.48, S 11.75. C15H15N3S

Calculated, %: C 66.88, H 5.61, N 15.60, S 11.90.  

         The purity of the synthesized 2,6-bis­(phenyl)hexahydro-1,3,5-triazine-4-tion is indicated with the method of thin - layer chromatography. Eluent is the mixture of isopropyl alcohol and hexane (3:1 ratio). The presence of the blot has explained with iodine smoke.

         IR spectrums have painted in Specord – 75 spectrometer with suspension prepared in Vaseline oil.

         NMR 1H and 13C spectrums are extracted in Bruker (300 Mhs) apparatus.

2,6-bis­(phenyl)hexahydro-1,3,5-triazine-4-tion`s 1H NMR spectrum (δ, m.h.): 5.67 (δ, 2H, 2CH); 7.30-7.48 (m, 10H, 2Ar); 10.49 (δ, 2H, 2NH); 11.41 (δ, 1H, NH). 13C NMR spectrum (δ, m.h.): 65.53 (2CH), 126.33 (4CH-Ar), 129.51 (4CH-Ar), 129.52 (2CH-Ar), 140.01 (2C-Ar), 173.18 (C=S).

RESULT AND DISCUSSION

Taken into consideration information showing above, by three – component condensation it has been synthesized hexahydro-1,3,5-triazine-4-tion and optimal condition for increasing the yield was also found. It is necessary to show that three – component cyclization reactions are complex reactions. It is normal to obtaining the accessory substances also with the basic substances. In obtaining reaction of hexahydro-1,3,5-triazine-4-tions by receiving accessory substances as azomarks result in reducing the yield. To increase the yield it is necessary to found optimal conditions. Thus, by using the better optimal digs was synthesized 2,6-bis­(phenyl)hexahydro-1,3,5-triazine-4-tion with 65% yield.

 

        

Three – component condensation reaction with thiourea, benzaldehyde and 33.5% water solution of ammonia was investigated to study the direction of the reaction by the scheme showed above and to increasing the yield of necessary substances.

Therefore analogical reactions were conducted and the fewer yields was got. This fact shows that three – component condensation on the basis of thioures, aliphatic or aromatic aldehydes and primary amines needs carrying out by different ways.

REFERENCES

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3.      Hearn, M. J.; Levy, F. Organic preparation and procedures int. 1984, 16, 3-4, 199-277.

4.      Chemical Encyclopedia. Pub-on “ Great Russian Encyclopedia” Moscow. 1995, 1248-1251.