The document describes the synthesis of phenytoin from benzoin. Benzil is first prepared from benzoin by treating it with nitric acid. Benzil is then reacted with urea in the presence of sodium hydroxide and ethanol through pinacolone rearrangement. This yields phenytoin, which is purified by acidification and recrystallization. The percentage yield and melting point of the synthesized phenytoin are determined.
The document describes the synthesis of phenytoin from benzoin. Benzil is first prepared from benzoin by treating it with nitric acid. Benzil is then reacted with urea in the presence of sodium hydroxide and ethanol through pinacolone rearrangement. This yields phenytoin, which is purified by acidification and recrystallization. The percentage yield and melting point of the synthesized phenytoin are determined.
The document describes the synthesis of phenytoin from benzoin. Benzil is first prepared from benzoin by treating it with nitric acid. Benzil is then reacted with urea in the presence of sodium hydroxide and ethanol through pinacolone rearrangement. This yields phenytoin, which is purified by acidification and recrystallization. The percentage yield and melting point of the synthesized phenytoin are determined.
The document describes the synthesis of phenytoin from benzoin. Benzil is first prepared from benzoin by treating it with nitric acid. Benzil is then reacted with urea in the presence of sodium hydroxide and ethanol through pinacolone rearrangement. This yields phenytoin, which is purified by acidification and recrystallization. The percentage yield and melting point of the synthesized phenytoin are determined.
The preparation of benzimidazole can be done by reaction between O-phenylene diamine with formic acid in presence of base i.e sodium hydroxide.It is a condensation type of reaction in which o-phenylene diamine condensed with formic acid to give benzimidazole with removal of two molecules of water.
NH2 N HCOOH NaOH NH2 N H O-phenylene diamine Benzimidazole
PROCEDURE:
Placed 27g of O-phenylenediamine in a round bottomed flask of 250ml and added 17.5g (16ml) of 90% formic acid. Heated the mixture on a water bath at 1000C for 2 hour. Cooled and added 10% sodium hydroxide solution slowly, with constant rotation of the flask, until the mixture is just alkaline to litmus. Filter off the synthesized crude benzimidazole by using the pump wash with ice cold water.
Recyrstallisation: Dissolved the synthesized product in 400ml of boiling water, added 2g of
decolorizing carbon and digest for 15minutes. Filter rapidly through Buchner funnel and a flask at the pump. Cool the filtrate to about 100C, filter off the benzimidazole, wash with 25ml of cold water and dry at 1000C. The yield of pure benzimidazole is 25g (85%), m.p 171- 1720C. CALCULATION
Here limiting reagent is O-phenylene diamine; hence yield should be calculated from its amount taken.
Molecular formula of O-phenylene diamine = C6H8N2
Molecular formula of benzimidazole = C7H6N2
Molecular weight of O-phenylene diamine = 108g/mole
Molecular weight of benzilidazole = 118g/mole
108g of O-phenylene diamine forms 118g benzimidazole
Therefore, 27g O-phenylene diamine will form………(X) g benzimidazole
X = (118 X 27)/108 = 29.5g
Theoretical yield = 29.5g
Practical yield = .......... g
% yield = (practical yield) X 100
(theoretical yield)
REPORT:
Benzimidazole was synthesized from O-phenylene diamine and submitted.
10. SYNTHESIS OF BENZOTRIAZOLE AIM:
To synthesize and submit benzotriazole from o-phenylene diamine and report its percentage yield.
REFERENCE:
1. Practical medicinal chemistry by Dr. Devala Rao, page no:35.
2. Comprehensive practical organic chemistry by V.K.Ahluwalia and Renu Aggarval, page no:121.
The sodium nitrite reacts with glacial acetic acid and liberates nitrous acid. The o-phenylene diamine reacts with nitrous acid and produce diazonium ion. When the structure and stereochemistry of diazonium ion are stable, intramolecular nitrogen coupling occurs and form benzotriazole directly.
NaNO2 + CH3COOH HNO2 + CH3COONa
sodiu acetic acid sodium acetate m nitrou nitrite s acid
+ NH2 N N + N H+ -H + HNO2 N - 2H2O N NH2 NH2 H o-phenylene Diazonium ion benzotriazole diamine CALCULATIONS Molecular weight of o-phenylene diamine =
Molecular weight of benzotriazole =
---- g of o-phenylene diamine gives -----g of benzotriazole
1g of o-phenylene diamine =
---- g of o-phenylene diamine =
Theoretical yield =
Practical yield =
𝑃𝑟𝑎𝑐𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 Percentage yield = x 100 𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
PROCEDURE:
Dissolve 1.3g of o-phenylenediamine in a mixture of 1.5ml of glacial acetic acid and 5ml water in a beaker. Stir until the solid dissolves, warm gently if necessary. Cool the solution to 150C. Stir well and add a solution of 2g of sodium nitrite in 2ml water. Reaction mixture become warm within 2-3 minutes and reaches a temperature of about 850C and then begins to cool. Colour changes from deep red to pale brown. Continue stirring for 15 minutes till the temperature fall about 35-400C. Thoroughly chill in ice bath for 30 minutes. Filter the product and wash with cold water.
USE:
Used in bulk drug industry as an important intermediate compound.
It is the basic nucleus present in anthelmintic drugs like mebendazole, thiabendazole etc.
REPORT:
Benzotriazole was prepared and submitted. The percentage yield was found to be --------- 11. SYNTHESIS OF 2,3-DIPHENYL QUINOXALINE
AIM:
To synthesize and submit 2,3-diphenyl quinoxaline from o-phenylenediamine and report its percentage yield.
REFERENCE:
1) Vogels textbook of practical organic chemistry,5th edition, page no:90.
2) Comprehensive practical organic chemistry by V.K.Ahluwalia and Renu Aggarwal, page no:123.
CHEMICAL REQUIREMENTS:
o-phenylenediamine, benzil, rectified spirit.
PRINCIPLE:
Quinoxalines are a type of heterocyclic compounds. They are also known as benzopyrazines.
N N
N N
benzopyrazine pyrazine
Generally quinoxaline is formed by the condensation of o-phenylenediamine with diketones.
Here 2,3-diphenyl quinoxaline is prepared by treating o-phenylenediamine with benzil.
CALCULATIONS Molecular weight of 2, 3-diphenyl quinoxaline =
Molecular weight of o-phenylene diamine =
----- g of o-phenylene diamine gives ----- g of 2, 3-diphenyl quinoxaline
1g of o-phenylene diamine =
----- g of o-phenylene diamine =
Theoretical yield =
Practical yield =
𝑃𝑟𝑎𝑐𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 Percentage yield = x 100 𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
PROCEDURE:
Add a solution of 1.1g of o-phenylenediamine in 8ml rectified spirit to a warm solution of
2.1g of benzil in 8ml rectified spirit. Warm the mixture for 30 minutes in a water bath. Add water dropwise until slight cloudiness persists. Cool the solution and filter the product.
USE:
Quinoxaline derivatives are used as antimicrobial agents like levomycin.
They are also used in dyes.
REPORT:
2,3-diphenyl quinoxaline was prepared and submitted.
The percentage yield was found to be ---------
12. SYNTHESIS OF PHENYTOIN
AIM:
To prepare and submit recrystallized dried product of phenytoin and calculate
(i) Percentage yield
(ii) Melting point
REFERENCE:
Medicinal chemistry theory and practical by and practical by Prof:K.Narayanan,Dr.Avjit
Phenytoin is 5,5-diphenyl imidazoline 2,4-dione.Benzil react with urea in the presence of
alkali and alcohol to give phenytoin by pinacolone rearrangement. PROCEDURE:
a) Preparation of Benzil from Benzoin:
Place 2g of benzoin and 5ml of concentrated HNO3 in a round bottom flask and heat on a boiling water bath till crystalline benzoin is replaced by oily benzil.Pour the mixture in to beaker of cold water with stirring the oily benzil crystallize in to yellow salt. b) Preparation of phenytoin from benzil: Place 1g benzil, 1g urea ,5ml 30% aqueous sodium hydroxide and 20ml ethanol in a round bottom flask which is attached to reflux condenser and boil for 2hours.Cool the mixture to attain room temperature.Pour the mixture to 100ml water and,mix and allow to stand for 15minutes.Filter to remove insoluble biproducts.Render the filtrate strongly acidic with concentrated HCl .Cool the filtrate in ice cold H2O.Filter the precipitate product dry and submit.
IDENTIFICATION Experiment Observation Inference
To the sample solution add White precipitate Presence of phenytoin
hydrochloric acid To the sample add pyridine Blue colour Presence of phenytoin and copper sulphate solution
REPORT:- 13. SYNTHESIS OF BENZOCAINE [ETHYL PARA AMINO BENZOATE]
AIM:
To synthesis recrystallized product of benzocaine from para amino benzoic acid and calculate
(i) Percentage yield
(ii) Melting point
REFERENCE:
Medicinal chemistry theory and practical by and practical by Prof:K.Narayanan,Dr.Avjit
Benzocaine is the ethyl ester of para amino benzoic acid(PABA).It can be prepaired from PABA and ethanol by fischer esterification.
COOCH 2CH3 COOH
+ CH3CH2OH
NH2 NH2
PABA Ethy para amino benzoate
PROCEDURE:
To a 100ml RB flask, add 8ml of ethanol, 4.12g of para amino benzoic acid(PABA) and 1.2ml of conc:H2SO4 keep the mixture under reflux for 1hour up on cooling reaction mixture sets to a solid mass of hydrochloride of ethyl para amino benzoate. Pour the hot solution in to excess of water(no hydrochloride) add Na2CO3 to the clear solution until it is neutral to litmus. Filter wash and dry the product.
IDENTIFICATION
EXPERIMENT OBSERVATION INFERENCE
To the sample solution add Deep red colour Benzocaine confirmed
sodium nitrite and con.HCl and cool the mixture. To this add a solution of beta naphthol in sodium hydroxide. Maintain the temperature at 0 to 5°
