Microwave assisted synthesis of some Traditional reactions:

Green chemistry approach

 

Akshay R. Yadav*, Shrinivas K. Mohite, Chandrakant S. Magdum

Department of Pharmaceutical Chemistry, Rajarambapu College of Pharmacy, Kasegaon,

Maharashtra, India-415404

*Corresponding Author E-mail: akshayyadav24197@gmail.com

 

ABSTRACT:

The microwave assisted organic reaction comes under green chemistry proved to be eco-friendly and higher yield. In present article we performed some organic reactions using microwave irradiation. This green processes have resulted through use of less or no catalyst, readily recyclable solvents and yield that are often higher than conventional method. Microwave heating produces heat in entire material in the same rate and the same time at a high speed and at a high rate of reaction. Microwave assisted synthesis has become an important tool to the medicinal chemist for rapid organic synthesis. The microwave reactions were performed using microwave assisted synthesis on microwave, the reactions were worked up extensively to obtain a pure form of product which was isolated using literature work-up procedures. The products were further recrystallized with suitable solvents. The reactions were monitored with TLC intermittently for microwave assisted synthesis and hourly for conventional method of synthesis.

 

KEYWORDS: Green chemistry, microwave irradiation, microwave reactions, microwave assisted reactions.

 

 


INTRODUCTION:

Synthesis of any chemical entities is major bottleneck in the drug discovery. Conventional methods for different chemical synthesis is very well documented and practiced. The methods for synthesis of organic compounds had continuously modified from the last 10 years1. The application of green chemistry principles and practices renders regulation, control, clean-up, and remediation of the environment2. In year 1855 Robert Bunsen invented the burner acts as energy source for heating reaction vessel this was latter superseded by isomental, oil bath but the drawback of the heating though method remains the same3. Microwave Assisted Organic Synthesis had developed in now years which has been considered superior to traditional heating4. Microwave assisted organic synthesis has as a new “lead” in the organic synthesis5.

 

The technique offers clean, simple, efficient, fast and economic for the synthesis of a number of organic molecules such reaction has new tool in the organic synthesis. Important advantage of this technology includes highly accelerated rate of the reaction time with an improvement in yield and quality of product6. This technique is considered as important approach toward green chemistry because this technique is more environments friendly and this technology is used in the laboratory and has the potential to have a large impact on the fields of combinatorial chemistry, screening, medicinal chemistry and drug development7. Conventional method of organic synthesis usually requires longer heating time, tedious apparatus setup which result in higher cost of process and the excessive use of solvents or reagents lead to environmental pollution8. Growth of green chemistry holds necessary potential for the reduction of by product, a reduction in the waste production and a lowering of energy costs9. Due to its ability to couple directly with reaction molecule and passing thermal conductivity leading to fast rise in the temperature microwave irradiation had used to improve many organic synthesis10. The Principle behind the heating in microwave oven is because interaction of charged particle of reaction material with electromagnetic wavelength of particular frequency11. The phenomena of the producing heat by electromagnetic irradiation are either by conduction or collision. All the wave energy changes its polarity from +ve to -ve with each cycle of wave this cause rapid orientation and reorientation of molecule which cause heating by collision12. If any charge particles of material are free to travel in the material for e.g. Electron in a sample of carbon a current will induce which will travel in phase with the field13. If charge particle are bound in regions of material the electric field component will cause them to move until opposing force balancing electric force14.

 

MATERIAL AND METHODS:

All reagents used were of synthetic grade. Melting point were recorded by open capillary method and are uncorrected. Experimental were performed using microwave synthesizer (catalyst). Comparitivelythe reactions were performed using conventional methods of synthesis using reflux condenser. The reactions were monitored with silica gel G at specific hours of synthesis. The time for the conventional and microwave assisted synthesis were noted.

 

Synthesis of 2,3-diphenyl quinoxaline15

A.   Microwave assisted reaction:

In 250ml RBF, dissolve 0.108g o-phenylenediamine and 0.21g benzil in 5ml ethanol, then subjected to microwave at 340 W for 10 min, then add water until a slight cloudiness persists and allow to cool. The above mixture was filtered at pump and then filtered solid was washed with cold water. Recrystallized with methanol. M.pt: 125-126C.

 

B.    Conventional synthesis:

Approximately 30 min of reflux is required to obtain the product using the equimolar quantities.

 

Scheme-I

 

Synthesis of 2,4,5-triphenyl-1-H imidazole15

A.      Microwave assisted reaction: In 250ml RBF, take benzil (0.5gm), ammonium acetate (0.5gm), benzaldehyde (0.5ml), glacial acetic acid (1ml) in round bottom flask, then subjected to microwave at 225 W for 15 min, allow reaction mixture to stand to room temperature to attain room temperature. Add 50ml of water and filter. Then solid mass is washed with toluene and recrystallized with methanol. M.pt: 274-278C

 

B.    Conventional synthesis:

Approximately 3 hrs of reflux is required to obtain the product using the equimolar quantities.

 

Scheme-II

 

Synthesis of Benzimidazole16

A.      Microwave assisted reaction: Place 2gm of o-phenylenediamine and add 2ml of 90% formic acid, in 250ml round bottom flask, then subjected to microwave at 225 W for 10 min, Cool and add 10% sodium hydroxide solution slowly with constant shaking until the mixture is just alkaline to litmus. Filter off the crude benzimidazole, wash with ice-cold water, drainwell and wash again with 10ml of cold water. Dissolve the product in hot water, add 1g of decolourising carbon and digest for 10 min. Filter rapidly at the pump through a preheated Buchner funnel and flask. Cool the filtrate to 10C, filter off the benzimidazole, wash with 25ml of cold water and dryat 100C. M.pt: 170-172C

 

B.      Conventional synthesis:

Approximately 2 hrs of reflux is required to obtain the product using the equimolar quantities

 

Scheme-III

 

Synthesis of acetanilide17

A.      Microwave assisted reaction:

Place 2ml of aniline and zinc dust (0.5gm) in acetic acid (10ml) round bottom flask then subjected to microwave at 225 W for 5min. Then carefully pour reaction mixture in cold water (20ml) in 100ml beaker with vigorous stirring. Slowly separate acetanilide cystals. After 10 min., filter the mixture with Buchner funnel, wash with water and dry. M.pt: 114-116C

 

B.      Conventional synthesis:

Approximately 2hrs of reflux is required to obtain the product using the equimolar quantities

 

Scheme-IV

 

Synthesis of 5,5-diphenyl hydantoin17

A.      Microwave assisted reaction:

Take a mixture 2 gmbenzil an0d 1.13gm urea were taken in ethanol, to it was 30% NaOH solution was added and the reaction was subjected to microwave 225 watt for 10 min, Intermittently TLCs were recorded. Reaction mixture was rendered acidic with conc. HCl. The product was filtered and washed with alcohol.M.pt: 293-295C

 

B.      Conventional synthesis:

Approximately 1hrs of reflux is required to obtain the product using the equimolar quantities.

 

Scheme-V

 

Synthesis of Ethyl Nicotinate17

A.      Microwave assisted reaction:

Take a mixture of 2gm of pure nicotinic acid, 5ml of absolute ethanol and 2ml of sulphuric acid. Cool the solution and pour it slowly on to 5g of crushed ice. Add sufficient ammonia solution to render the resulting solution strongly alkaline, irradiate the mixture under microwave, 340 watt for 3 min. M.pt: 9-11C

 

B.      Conventional synthesis:

Approximately 30 min of reflux is required to obtain the product using the equimolar quantities.

 

Scheme-VI

 

RESULT AND DISCUSSION:

Table 1 shows comparision of the time taken by microwave assisted synthesis and % yield of compound.

 

Table 1: Comparision of the time taken by Microwave irradiation and time taken by conventional synthesis.

Name of the compound

% yield from

MWI

Time taken by conventional synthesis in min hours

Time taken by MWI in minutes

2,3-diphenyl quinoxaline

94.45

30 min

10

2,4,5-triphenyl-1-H imidazole

84.23

3 hrs

15

Benzimidazole

90.12

2 hrs

10

acetanilide

78.65

2 hrs

5

5,5-diphenyl hydantoin

92.45

1 hrs

10

Ethyl Nicotinate

80.76

30 min

3

 

CONCLUSION:

Microwave assisted synthesis is faster, better and safer green chemistry approach for the traditional reactions. The time taken for the synthesis is drastically reduced by the microwave assisted synthesis. Several named reactions were carried out using microwave assisted synthesis. This technique offers clean, simple, efficient, fast and economic for the synthesis of a number of organic molecules such reaction has new tool in the organic synthesis. Important advantage of this technology includes highly accelerated rate of the reaction time with an improvement in yield and quality of product.

 

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Received on 08.04.2020                    Modified on 24.04.2020

Accepted on 05.05.2020                   ©AJRC All right reserved

Asian J. Research Chem. 2020; 13(4):275-278.

DOI: 10.5958/0974-4150.2020.00053.X