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