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Chemotherapeutics Laboratory Experiments Report Biology

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In order to execute Parallel synthesis and Biginelli reaction, foremost, 0.70gms 3-Chlorobenzyldehyde, 1.08gms alkyl acetoacetate, 0.37gms methyl carbamide and 2ml ethyl alcohols were added to a 7ml reaction tubing incorporating a magnetic scaremonger.

Afterwards, 2-3 beads of conc. HCl were added ( Use in Hood ) into the mixture and the slurry refluxed in the Greenhouse Parallel reactor for 2 h. The reaction was cooled to 0oC and the attendant precipitate collected. For better precipitates, merchandise may be farther purified by recrystallization from ethyl alcohol.

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Balanced reaction Scheme

Alkyl acetoacetate

3-Chlorobenzyldehyde

1- ( Aminocarbonyl ) -6- ( 3-chlorophenyl ) -1,2,3,6-tetrahydro-4-methyl-2-oxo-5-pyrimidinecarboxylic acerb 1-methylethyl ester/ SQ 32926

Methyl carbamide

Melting point: 94oC

Output: 0.30gm

NMR Data ( Parallel Synthesis )

H NMR Data

2.468 ( 1, 3H ) , 1.433 ( 2, 3H, J=6.904 ) , 1.433 ( 3, 3H, vitamin D, J=6.904 ) , 7.345 ( 9, 1H, J=8.085, J=8.057, J=4.353 ) , 7.251 ( 10, 1H, J=8.057, J=1.671, J=1.561 ) , 7.427 ( 11, 1H, J=8.085, J=1.671, J=1.501 ) , 7.521 ( 12, 1H, J=4.353, J=1.561, J=1.501 ) , 4.771 ( 22, 1H, J=6.904 ) , 5.885 ( 23, 1H )

Biginelli Reaction

For Biginelli reaction, 532mg benzaldehyde, 968µl ethyl acetoacetate, 370mg N-methyl carbamide and 5ml ethyl alcohols were added to a 50ml unit of ammunition underside flask incorporating a magnetic scaremonger. Further, 2-3 beads of conc. HCl were added and the mixture refluxed for 2 h. The reaction was cooled to 0oC and the attendant precipitate collected. For better precipitates, merchandise may be farther purified by recrystallization from ethyl alcohol.

Oxygen

Hydrogen

C

Oxygen

2

Tocopherol

T

Meter

vitamin E

Oxygen

Nitrogen

Hydrogen

2

Oxygen

Nitrogen

Hydrogen

2

Nitrogen

Hydrogen

Nitrogen

Hydrogen

Oxygen

C

Oxygen

2

Tocopherol

T

Meter

vitamin E

Balanced reaction Scheme

N-methyl carbamide

Ethyl acetoacetate

Benzaldehyde

HCl, EtOH

Dihydropyrimidinone

Melting point: 176oC

Output: 0.60gm

NMR Data ( Biginelli reaction )

H NMR tabulate

0.826 ( 1, 3H, J=6.614 ) , 1.133 ( 2, 3H, J=6.651 ) , 7.222 ( 4, 1H, J=7.722, J=1.262, J=1.261 ) , 7.198 ( 5, 1H, J=7.911, J=7.722, J=5.336, J=0.000 ) , 7.198 ( 6, 1H, J=7.910, J=7.722, J=5.338, J=0.000 ) , 7.252 ( 7, 1H, J=7.911, J=5.338, J=1.262, J=0.000 ) , 7.252 ( 8, 1H, J=7.910, J=5.336, J=1.261, J=0.000 ) , 1.275 ( 9, 2H, J=6.614, J=2.589 ) , 3.633 ( 14, 1H, J=6.651, J=3.270 ) , 1.990 ( 15, 1H, J=3.280, J=3.270, J=2.589 ) , 5.434 ( 16, 1H, vitamin D, J=3.280 )

C NMR tabulate

14.5631, 16.5469, 30.2236, 39.8088, 40.0187, 40.2285, 52.9610, 60.0474

Experiment 2

Suzuki Cross Coupling Chemical reactions: Synthesis of Unsymmetrical Biaryls

Date of experiment:

Table of reagents:

Name/chemical expression and/or construction

4-Bromoacetophenone/ C6H4BrCOCH3

4?-Bromoacetophenone 98 %

Phenyl Boronic acid/C6H7BO2

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Triphenylphosphine/PPh3

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N-propanol and Palladium acetate 1-Propanol anhydrous, 99.7 %

Palladium ( II ) acetate reagent class, 98 %

Sums ( mmol, milligram

and milliliter )

1gm 4-bromoacetophenone

0.69 phenyl boronic acid

26mg triphenylphosphine

10ml n-propanol and 7mg Pd ethanoate

Molecular weight, figure of moles of the reactants

4-bromoacetophenone

Mw=199.04, 5.02mmol

Phenyl boronic acid

Mw=121.93, 5.68mmol

Triphenylphosphine

Mw=262.29, 97.6µmol

Warning about dissolvers

Irritant, Avoid tegument, oculus contact, harmful if inhaled etc.

Procedure

For Suzuki cross matching reactions, 1gm of the aryl halide, 0.692gm of the arylboronic acid and 10ml of n-propanol were added to a 100ml unit of ammunition bottomed flask equipped with a magnetic splash saloon and capacitor. The capacitor has been set up on the flask with affiliated balloon. Then, 7.2mg Pd ethanoate, 25.6mg triphenylphosphine as solid and 3.25ml 2M aqueous Na carbonate were added along with 2ml deionised H2O. Let the system to purge with N by somewhat opening the flask/condenser articulation for a few proceedingss. Heated the reaction to reflux under a nitrogen environment until approx. 3 hours.

At room temperature, 30ml H2O was added and mixture has stir for 5min. in the air. Then, reaction was diluted with 50ml ethyl ethanoate and transferred it to a separating funnel. Two beds were separated and aqueous bed has re-extracted with 50ml ethyl ethanoate. Afterwards, combine the organic infusions and rinse them with a 5 % Na carbonate solution ( 2 – 20ml ) and 10ml seawater consecutive. Organic stage was so transferred to a conelike flask equipped with a magnetic splash saloon and 0.50gm activated wood coal and 1g Na sulfate has been added. Slurry has stirred for 10min. so solution was filtered. Concentrate the ensuing pale xanthous filtrate under decreased force per unit area to give the biaryl merchandise as a solid. For crystals, slurry was washed with ~2ml methyl alcohol.

Melting point, IR spectra has been recorded and NMR information was collected.

Balanced reaction Scheme

aq. Na2CO3, n-propanol

Pd ( OAc ) 2, PPh3

Phenyl boronic acid

4-Bromoacetophenone

Biaryl ketone

Melting point: 120oC

Output: 0.1gm

NMR Data

H NMR Tabulate:

2.380 ( 1, 3H ) , 7.522 ( 3, 1H, J=7.171, J=7.156, J=1.317, J=1.246 ) , 7.415 ( 4, 1H, J=7.938, J=7.156, J=1.502, J=1.430 ) , 7.450 ( 5, 1H, J=8.083, J=7.171, J=1.502, J=1.499 ) , 7.700 ( 6, 1H, J=7.938, J=1.499, J=1.471, J=1.317 ) , 7.799 ( 7, 1H, J=8.083, J=1.471, J=1.430, J=1.246 ) , 7.688 ( 8, 1H, J=8.649, J=1.647, J=1.065 ) , 7.682 ( 9, 1H, J=8.643, J=1.647, J=0.995 ) , 7.724 ( 10, 1H, J=8.649, J=1.716, J=0.995 ) , 7.769 ( 11, 1H, J=8.643, J=1.716, J=1.065 )

C NMR Tabulate:

26.7820, 76.8178, 77.1420, 77.4567, 127.3209, 127.3685, 128.3412, 129.0564, 135.9224, 139.9562, 145.8685, 197.8878

Experiment 3

Resolution of a i??-Methylbenzyl Amine

Date of experiment:

Table of reagents:

Name/chemical expression and/or construction

( 2R, 3R ) -Tartaric acid/HO2CCH ( OH ) CH ( OH ) CO2H

L- ( + ) -Tartaric acerb ACS reagent, ?99.5 %

i??-Methylbenzyl Amine/C6H5CH ( CH3 ) NH2

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Methanol/CH3OH

Sums ( mmol, milligram

and milliliter )

1.60gm ( 2R, 3R ) -Tartaric acid

1.40mliˆ i??-Methylbenzyl Amine

50ml Methanol

Molecular weight, figure of moles of the reactants

( 2R, 3R ) -Tartaric acid Mw=150.0

i??-Methylbenzyl Amine Mw=121.18

Warning about dissolvers

Irritant, Avoid tegument, oculus contact, harmful if inhaled, usage in fume goon etc.

Procedure

Part 1: ( 2R, 3R ) -tartaric acid and methyl alcohol were added to a 100ml unit of ammunition underside flask. Solution was heated with capacitor for few proceedingss. Measured 1.40ml of racemic i??-Methylbenzyl Amine in to a little vial utilizing a disposable syringe. Flask was removed from heating and so i??-Methylbenzyl Amine was easy added with a Pasteur pipette. Slurry was once more heated with capacitor and was refluxed gently for ~15 proceedingss. Solution so has positioned under room temperature and placed into the closet for 24 hours.

Part 2: less soluble diastereoisomer, ( S ) -iˆ i??-methylbenzylammonium H ( 2R,3R ) -tartrate was collected, via vacuity filtration and the crystals were rinsed with approximately 5 milliliters of ice-cold methyl alcohol. Then crystals were transferred to a conelike flask and H2O was added to fade out the solid. Then dropwise 6M NaOH solution was added to fade out the crystals. Organic bed has separated from dividing funnel with diethyl quintessence. Combined organic bed so dried over Mg sulfate and solution was filtered in pre-tared flask. Solvent was removed on the rotary evaporator and mass was recorded of the stray aminoalkane.

To mensurate the Optical Rotation: i??-Methylbenzyl Amine and ethyl alcohol were weighted into a flask. Then sample placed into the polariscope and rotary motion -i??- the mark ( + or – ) and temperature were recorded. The specific rotary motion, [ i?? ] D Temp was calculated.

Specific rotary motion of the merchandise: Optical rotary motion is measured with an instrument called a polariscope. There is a additive relationship between the ascertained rotary motion and the concentration of optically active compound in the sample. There is a non-linear relationship between the ascertained rotary motion and the wavelength of visible radiation used. Specific rotary motion is calculated utilizing either of two equations, depending on the sample you are mensurating:

For pure liquids:

[ alpha ] _lambda^T = frac { alpha } { fifty imes
ho }

In this equation, cubic decimeter is the way length in decimetres, and ? is the denseness of the liquid in g/mL, for a sample at a temperature T ( given in grades Celsius ) and wavelength ? ( in nanometres ) . The mark of the rotary motion ( + or – ) is ever given.

=-140 optical rotary motion, cell length 0.02 diabetes mellitus, sample 10 milligram, in 10 ml solution. Optical rotation=-7000o cm3dm-1g-1 [ ? ]

Output: 0.02ml

Boiling point: 275oC

Balanced reaction Scheme

H2O, NaOH

i??-Methylbenzyl Amine

S-methyl benzyl aminoalkane

Methanol

( 2R, 3R ) -Tartaric acid

NMR Data

H NMR tabulate

1.244 ( 1, 3H, J=6.470 ) , 7.316 ( 3, 1H, J=7.706, J=1.168 ) , 7.331 ( 4, 1H, J=7.712, J=7.706, J=4.830, J=0.000 ) , 7.331 ( 5, 1H, J=7.712, J=7.706, J=4.829, J=0.000 ) , 7.289 ( 6, 1H, J=7.712, J=4.829, J=1.168, J=0.000 ) , 7.289 ( 7, 1H, J=7.712, J=4.830, J=1.168, J=0.000 ) , 4.253 ( 9, 1H, J=6.470 )

Experiment 4

The synthesis of Alkenes: The Wittig and related Chemical reactions

Date of experiment:

Table of reagents:

Name/chemical expression and/or construction

Triethylphosphono-acetate/ ( C2H5O ) 2P ( O ) CH2CO2C2H5

Triethyl phosphonoacetate 98 %

Benzyldehyde/C6H5CHO

Benzaldehyde purified by redistillation, ?99.5 %

Sums ( mmol, milligram

and milliliter )

1gm Triethylphosphono-acetate

0.47gm Benzaldehyde

Molecular weight, figure of moles of the reactants

Triethylphosphono-acetate Mw=224.19, 4.46mmol

Benzaldehyde Mw=106.12, 4.46mmol

Warning about dissolvers

Irritant, Avoid tegument, oculus contact, harmful if inhaled, usage in fume goon etc.

Procedure

Preparation of ( E ) -Ethyl cinnamate

To a mixture of triethylphosphono-acetate in dry THF was added n-butyl Li at 0oC. the mixture was stirred for 30 proceedingss so benzaldehyde was added and the mixture stirred for a farther 2 H so allowed to warm to room temperature. After thining with ethyl ethanoate, combined organic bed were dried and the dissolver was evaporated in vacuo to give a xanthous oil. Purification by column chromatography gave ( E ) -Ethyl cinnamate a colorless oil.

Balanced reaction Scheme

n-BuLi, THF

( Tocopherol ) -Ethyl cinnamate

Benzyldehyde

Triethylphosphono-acetate

Melting point: 8oC

Output: 0.2gm

NMR informations

H NMR tabulate

1.217 ( 1, 3H, J=7.115 ) , 6.647 ( 3, 1H, J=16.268 ) , 7.726 ( 4, 1H, J=16.268 ) , 7.455 ( 5, 1H, J=7.243, J=1.494 ) , 7.433 ( 6, 1H, J=7.952, J=7.243, J=0.840, J=0.000 ) , 7.433 ( 7, 1H, J=7.951, J=7.243, J=0.805, J=0.000 ) , 7.538 ( 8, 1H, J=7.952, J=1.494, J=0.805, J=0.000 ) , 7.538 ( 9, 1H, J=7.951, J=1.494, J=0.840, J=0.000 ) , 4.117 ( 10, 2H, Q, J=7.115 )

C NMR tabulate

166.5914, 144.2484, 134.1211, 129.061, 128.5520, 127.7319, 117.9288, 77.3242, 77, 76.6853, 60.1307, 14.0047

Cite this Chemotherapeutics Laboratory Experiments Report Biology

Chemotherapeutics Laboratory Experiments Report Biology. (2017, Jul 12). Retrieved from https://graduateway.com/chemotherapeutics-laboratory-experiments-report-biology-essay/

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