The Synthesis Of A Series Of Compounds Biology Essay

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- The synthesis of a series of compounds by 1,3-Dipolarcyclo addition involves same procedure with some variations ie., use of different quantities of different derivatives of benzaldehyde for the synthesis of compounds.

Synthesis of 3,5-Diphenyl Isoxazoline:

Chemicals Required:

Benzaldehyde - 5.1ml

Hydroxylamine Hydrochloride - 4.2gms

Sodium hydroxide - 3.5gms

Styrene - 2.9ml

Triethylamine - 0.3ml

Sodium hypochlorite (ca, 10% available chlorine)- 25ml

Glacial acetic acid

Diethyl ether

Dichloromethane

Step 1- Preparation of Benzaldehyde Oxime:

Working in a fume cupboard, Sodium Hydroxide(3.5gms) was dissolved in water in a 100ml conical flask by stirring with a magnetic stirrer and the solution was left to cool. 0.5gms of Benzaldehyde was added into the flask following 0.5gms of Hydroxylamine Hydrochloride. The flask was then stoppered and mixed vigorously for 5 minutes. The stopper was removed and further proportions of Benzaldehyde and Hydroxylamine Hydrochloride were added by maintaining a time interval of 5 minutes. The mixture was stirred until the solution became pale yellow with no almond smell.

The above obtained solution was neutralized by the addition of Glacial acetic acid slowly using a Pasture pipette. The mixture was cooled and extracted with Diethyl ether (2-30 ml). The organic layer was collected and dried over Magnesium Sulphate with suction. The resultant pure organic layer was collected in a pre-weighed round bottom flask and is evaporated under pressure by using a rotary evaporator. The end product obtained was a yellow colour oil.

Step 2- 1,3- Dipolar Cycloaddition:

Styrene and Triethylamine were dissolved in 15ml of Dichloromethane in a 100ml conical flask with the help of a magnetic stirrer. Sodium hypochlorite (25ml) solution was added to the mixture and cooled in an ice-bath with stirring. Benzaldehyde oxime(2.5gms) was added drop wise over fifteen minutes and the mixture was stirred vigorously for 45 minutes.

The mixture was transferred into a separating funnel and the organic layer was separated into a clean beaker. The aqueous layer was extracted with 15ml of dichloromethane. The organic extracts were combined and dried over Magnesium Sulphate with suction. Then the solvent is evaporated under pressure using a rotary evaporator and the resultant crystalline powder was collected, weighed and purified by recrystallization from ethanol. The product obtained after recrystallization were white crystals of 3,5-Diphenyl isoxazoline with melting point 83.5-85.6.

Synthesis of 3-(4-methoxy phenyl)-5-phenyl Isoxazoline:

Chemicals Required:

4-Methoxy benzaldehyde - 5.5gms

Hydroxylamine Hydrochloride - 4.2gms

Sodium hydroxide - 3.5gms

Styrene - 2.9ml

Triethylamine - 0.3ml

Sodium hypochlorite (ca, 10% available chlorine)- 25ml

Glacial acetic acid

Diethyl ether

Dichloromethane

Step 1- Preparation of Benzaldehyde Oxime:

Working in a fume cupboard, Sodium Hydroxide(3.5gms) was dissolved in water in a 100ml conical flask by stirring with a magnetic stirrer and the solution was left to cool. 0.5gms of 4-Methoxy benzaldehyde was added into flask following 0.5gms of Hydroxylamine Hydrochloride. The flask was then stoppered and then mixed vigorously for 5 minutes. The stopper was removed and further proportions of 4-Methoxy benzaldehyde and Hydroxylamine Hydrochloride were added by maintaining a time interval of 5 minutes. The mixture was stirred until the solution became pale yellow with no almond smell.

The above obtained solution was neutralized by the addition of Glacial acetic acid slowly using a Pasture pipette. The mixture was cooled and extracted with Diethyl ether (2-30 ml). The organic layer was collected and dried over Magnesium Sulphate with suction. The resultant pure organic layer was collected in a pre-weighed round bottom flask and is evaporated under pressure by using a rotary evaporator. The end product obtained was a yellow powder.

Step 2- 1,3- Dipolar Cycloaddition:

Styrene and Triethylamine were dissolved in 15ml of Dichloromethane in a 100ml conical flask with the help of a magnetic stirrer. Sodium hypochlorite (25ml) solution was added to the mixture and cooled in an ice-bath with stirring. 4-Methoxy benzaldehyde oxime(2.5gms) was added drop wise over fifteen minutes and the mixture was stirred vigorously for 45 minutes.

The mixture was transferred into a separating funnel and the organic layer was separated into a clean beaker. The aqueous layer was extracted with 15ml of dichloromethane. The organic extracts were combined and dried over Magnesium Sulphate with suction. Then the solvent is evaporated under pressure using a rotary evaporator and the resultant crystalline powder was collected, weighed and purified by recrystallization from ethanol. The product obtained after recrystallization were white crystals of 3-(4-methoxy phenyl)-5-phenyl isoxazoline with melting point 110.3-114.8.

Synthesis of 3-(4-Nitro phenyl)-5-phenyl isoxazoline:

Chemicals Required:

4-Nitro benzaldehyde - 7.1gms

Hydroxylamine Hydrochloride - 4.2gms

Sodium hydroxide - 3.5gms

Styrene - 2.9ml

Triethylamine - 0.3ml

Sodium hypochlorite (ca, 10% available chlorine)- 25ml

Glacial acetic acid

Diethyl ether

Dichloromethane

Step 1- Preparation of Benzaldehyde Oxime:

Working in a fume cupboard, Sodium Hydroxide(3.5gms) was dissolved in water in a 100ml conical flask by stirring with a magnetic stirrer and the solution was left to cool. 0.5gms of 4-Nitro benzaldehyde was added into flask following 0.5gms of Hydroxylamine Hydrochloride. The flask was then stoppered and mixed vigorously for 5 minutes. The stopper was removed and further proportions of 4-Nitro benzaldehyde and Hydroxylamine Hydrochloride were added by maintaining a time interval of 5 minutes. The mixture was stirred until the solution becomes no almond smell.

The above obtained solution was neutralized by the addition of Glacial acetic acid slowly using a Pasture pipette. The mixture was cooled and extracted with Diethyl ether (2-30 ml). The organic layer was collected and dried over Magnesium Sulphate with suction. The resultant pure organic layer was collected in a pre-weighed round bottom flask and is evaporated under pressure by using a rotary evaporator. The end product obtained was a yellow powder.

Step 2- 1,3- Dipolar Cycloaddition:

Styrene and Triethylamine were dissolved in 15ml of Dichloromethane in a 100ml conical flask with the help of a magnetic stirrer. Sodium hypochlorite (25ml) solution was added to the mixture and cooled in an ice-bath with stirring. 4-Nitro benzaldehyde oxime(2.5gms) was added drop wise over fifteen minutes and the mixture was stirred vigorously for 45 minutes.

The mixture was transferred into a separating funnel and the organic layer was separated into a clean beaker. The aqueous layer was extracted with 15ml of dichloromethane. The organic extracts were combined and dried over Magnesium Sulphate with suction. Then the solvent is evaporated under pressure using a rotary evaporator and the resultant crystalline powder was collected, weighed and purified by recrystallization from ethanol. The product obtained after recrystallization were white crystals of 3-(4-Nitro phenyl)-5-phenyl isoxazoline with melting point 136.4-141.8.

Synthesis of 3-(4-Methyl phenyl)-5-phenyl isoxazoline:

Chemicals Required:

4-Methyl benzaldehyde - 7.1gms

Hydroxylamine Hydrochloride - 4.2gms

Sodium hydroxide - 3.5gms

Styrene - 2.9ml

Triethylamine - 0.3ml

Sodium hypochlorite (ca, 10% available chlorine)- 25ml

Glacial acetic acid

Diethyl ether

Dichloromethane

Step 1- Preparation of Benzaldehyde Oxime:

Working in a fume cupboard, Sodium Hydroxide(3.5gms) was dissolved in water in a 100ml conical flask by stirring with a magnetic stirrer and the solution was left to cool. 0.5gms of 4-Methyl benzaldehyde was added into flask following 0.5gms of Hydroxylamine Hydrochloride. The flask was then stoppered and mixed vigorously for 5 minutes. The stopper was removed and further proportions of 4-Methyl benzaldehyde and Hydroxylamine Hydrochloride were added by maintaining a time interval of 5 minutes. The mixture was stirred until the solution becomes no almond smell.

The above obtained solution was neutralized by the addition of Glacial acetic acid slowly using a Pasture pipette. The mixture was cooled and extracted with Diethyl ether (2-30 ml). The organic layer was collected and dried over Magnesium Sulphate with suction. The resultant pure organic layer was collected in a pre-weighed round bottom flask and is evaporated under pressure by using a rotary evaporator. The end product obtained was a yellow powder.

Step 2- 1,3- Dipolar Cycloaddition:

Styrene and Triethylamine were dissolved in 15ml of Dichloromethane in a 100ml conical flask with the help of a magnetic stirrer. Sodium hypochlorite (25ml) solution was added to the mixture and cooled in an ice-bath with stirring. 4-Methyl benzaldehyde oxime(2.5gms) was added drop wise over fifteen minutes and the mixture was stirred vigorously for 45 minutes.

The mixture was transferred into a separating funnel and the organic layer was separated into a clean beaker. The aqueous layer was extracted with 15ml of dichloromethane. The organic extracts were combined and dried over Magnesium Sulphate with suction. Then the solvent is evaporated under pressure using a rotary evaporator and the resultant crystalline powder was collected, weighed and purified by recrystallization from ethanol. The product obtained after recrystallization were white crystals of 3-(4-Methyl phenyl)-5-phenyl isoxazoline with melting point 108.5- 111.4.

Synthesis of 3-(4-Chloro phenyl)-5-phenyl isoxazoline:

Chemicals Required:

4-Chloro benzaldehyde

Hydroxylamine Hydrochloride - 4.2gms

Sodium hydroxide - 3.5gms

Styrene - 2.9ml

Triethylamine - 0.3ml

Sodium hypochlorite (ca, 10% available chlorine)- 25ml

Glacial acetic acid

Diethyl ether

Dichloromethane

Step 1- Preparation of Benzaldehyde Oxime:

Working in a fume cupboard, Sodium Hydroxide(3.5gms) was dissolved in water in a 100ml conical flask by stirring with a magnetic stirrer and the solution was left to cool. 0.5gms of 4-Chloro benzaldehyde was added into flask following 0.5gms of Hydroxylamine Hydrochloride. The flask was then stoppered and mixed vigorously for 5 minutes. The stopper was removed and further proportions of 4-Chloro benzaldehyde and Hydroxylamine Hydrochloride were added by maintaining a time interval of 5 minutes. The mixture was stirred until the solution becomes no almond smell.

The above obtained solution was neutralized by the addition of Glacial acetic acid slowly using a Pasture pipette. The mixture was cooled and extracted with Diethyl ether (2-30 ml). The organic layer was collected and dried over Magnesium Sulphate with suction. The resultant pure organic layer was collected in a pre-weighed round bottom flask and is evaporated under pressure by using a rotary evaporator. The end product obtained was a yellow powder.

Step 2- 1,3- Dipolar Cycloaddition:

Styrene and Triethylamine were dissolved in 15ml of Dichloromethane in a 100ml conical flask with the help of a magnetic stirrer. Sodium hypochlorite (25ml) solution was added to the mixture and cooled in an ice-bath with stirring. 4-Chloro benzaldehyde oxime(2.5gms) was added drop wise over fifteen minutes and the mixture was stirred vigorously for 45 minutes.

The mixture was transferred into a separating funnel and the organic layer was separated into a clean beaker. The aqueous layer was extracted with 15ml of dichloromethane. The organic extracts were combined and dried over Magnesium Sulphate with suction. Then the solvent is evaporated under pressure using a rotary evaporator and the resultant crystalline powder was collected, weighed and purified by recrystallization from ethanol. The product obtained after recrystallization were white crystals of 3-(4-Chloro phenyl)-5-phenyl isoxazoline with melting point 135.9- 140.7.

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