PREPARATION OF SODIUM 1(4-OXO-3-THIOUREIDOQUINAZOLIN-2-YL)-HEPTA DECANE-1-SULFONATE

INTRODUCTION.
Several anionic surfactants containing both the thiophene and pyrrole nucleus as well as a long alkyl chain with a sulphonic or carboxylic hydrophillic groups are reported to possess a wide spectem of surface activity. Promted by these observations and in continuation of our investigations on biologically active derivaties among six membered hetero cycles it was considered of interest to extend the previous studies to prepare a new series of quinazoline derivaties bearing (long alkyl chain with sulphonic acid hydrophillic center) in a single moleculer frame work likely to constitute new biologically active anionc surfactanta compounds which may

RESULTS AND DISCUSSION.

The required sodium 1-(4-oxo-4H-benzo[d] [1,3]oxazin2-yl)heptadecane-1-sulfonate was synthesised by refluxing sodium 1-chloro carbonyl heptadecane-1-sulfonate with anthranillic acid in boiling pyridine. 1-(4-oxo-4H-benzo[d][1,3]oxazin-2yl)heptadecane-1-sulfonate with thio semicarbazide in boiling pyridine gave sodium 1(4-oxo-3-thioureido-quinazolin-2-yl)heptadecane-1sulfonate which is cyclised by fusion above its melting point to yield trizolo quinazoline derivative

REACTION SCHEME

C O

OH

SOCl2

C O

Cl

COOH NH2

O O N R

H2N HN C S

NH2

O N N R NH

S C NH2

SURFACE ACTIVE PROPERTIES.

Anionic surface active agents are very distributed throughout science, technology,and everyday life. Examples; washing, wetting out textile materials,the preparation of dispersions and emulsions, the application of agricultural and harticultural sprays and wide variety of special uses. The surface properties (surface &interfacial tension,kraft point,wetting time ,foamingheight and emulsion stability) of purified compounds were investigated at 30degrecentigrade in distilled water. The Ca++ stability and stability to hydrolysis and biodegradability properties were also studied.

SURFACE AND INTERFACIAL PROPERTIES.

The synthesised anionic surfactants with hetero cyclic moiety showed lower values for surface tension and interfacial tension.It was found that the decrease of values of surface and interfacial tension might be due to the electrostatic repulsion between the ionized molecules.The results indicate that all the synthesised products have pronounced surface activity. Surface and inter facial property our compound are 35&8.7

KRAFT POINT.
The kraft point mesurments proved that the higher the molecular weight the higher the kraft point value. Kraft point of our compound is 22.

WETTING TIME. Wetting times of the tested surfactants were determined by measuring the sinking time in seconds of a gram cotton skin in the surfactant solution.The results show that the products were very effective wetting agents in distilled water solutions .It is hoped that they wil find a wide range of applications in the textile industry. Wetting time in sec of our compound

FOAMING HEIGHT.
The results revealed that the new compounds yield low foam. The low foaming power compounds have application in the dyeing and auxillary industries. Foaming height of our compound in mm is 170.

EMULSION STABILITY.
In many textile processes such as scouring and dyeing .It is necessary to introduce surfactants into the bath to remove oily impurities from the fiber. The prepared compounds useful in dye baths in the textile industry and as emulsion paints. Emulsion stability is 320.

Ca++ STABILITY.
High calicum stability values show that the prepared compounds can be used in hard water. Ca++ stability is 1350.

STABILITY TOWARDS HYDROLYSIS.

The prepared anionic surfactants are moderately stable in basic medium. Stability to hydrolysis in min; sec 44;0.

BIODEGRADABILITY.
Each experiment was repeated at least 3 times and the results are repeated as averages of 3 values. The results indicate that compound undergo substantial degradation. Biodegradability of compound is 1st day 41. 2nd day 50. 3rd day 58. 4th day 67. 5th day 75. 6th day 92. 7th day _

ANTIMICROBIAL ACTIVITY.
The compounds was tested using the cup-plate method. The compound were tested against gram positive ,gram negative bacteria and selected fungi. Bacillus sublitis Activity ++ ,MIC 125. ESCHERICHIA COI Activity +,MIC 250.

 Aspergillus niger Activity ++ , MIC 250. CANDIDA ALBICAM. Activity + ,MIC 250. MIC=minimum inhibitory concentration. (+)=weak activity. (++)=moderate activity.

EXPERIMENTAL PROCEDURE.
Preparation of sodium 1-(4-oxo-4Hbenzo[d][1,3]oxazin-2-yl heptadecane sulfonate. A solution of acid chloride 5ml and anthranillic acid 5ml in dry pyridine 30ml was refluxed for 3 hr . The reaction mixture was cooled and poured in to cold diluted Hcl .The solid that separated was collected by filtration and recrystallised from benzene to give above compound.yield 75%.

PREPARATION OFSODIUM1-(4OXO-3THIOUREIDOQUINAZOLIN-2YL)HEPTADECANE SULFONATE.

Above solution 7ml and thiosemicarbazide 7 ml was heated in boiling pyridine20ml under reflux for 3hr then poured into water. The separated solid after cooling was collected by filtration and crystalised from ethanol n give above compound .yield 70%.