DHANRAJ
DHANRAJ
DHANRAJ
Science
CollegeTaloda -425413
A
SHORT RESEARCH
PROJECT FOR M.sc.-ll
IN
(ORGANIC
CHEMISTRY)
C.H.C.Arts, S.G.P. Commerce and B.B.J.P. Science
CollegeTaloda -425413
DEPARTMENT OF CHEMISTRY
Thanking all !
1 Abstract
2 Introduction
3 Experimental
5 Recrystallization
6 Application
7 Conclusion
8 References
ABSTRACT
The general lipid-lowering action of the N-substituted phthalimide derivatives reported
here in, as well as activity of Potassium phthalimide, implicates the phthalimide moiety as
possessing Hypolipidemic activity in compounds containing substituents with chain lengths of
four carbon or oxygen atoms showed the best hypolipidemic activity in the series tested. Tests
involving 1-N-phthalimidobutan-3-one demonstrated a dependent hypolipidemic action free of
Estrogenic side effects with no deposition of cholesterol in body organs with high therapeutic
index. Further work on the hypolipidemic activity of Phthalimido as well as other imido
compounds is underway.
Keywords:-
Part A
1)Phthalic anhydride
2) Acetic acid (solvent)
3)Urea
4) Thiourea
Appratus :-
Round bottom Flask
Sand Bath
SYNTHESIS OF N - SUBSTITUTED PHTHALIMIDE
INTRODUCTION
Epilepsy is a relatively common neurological condition affecting 0.5 -1% of worlds populations. The classical
Antiseptics drugs comprise Phenytoin, Phenobarbital, Carbamazepine, valproic acid and various benzodiazepines
still widely utilized in the treatment of the various forms of epilepsy. In recent years several new drugs have been
employed eg. Felbamate, fospheny toin gabapentin, tiagabine, topiramate, vigabatrin and zonisamide.
Among the compounds tested for anticonvulsant activity are phthalimide derivative based on the
structure activity relationship for 4 amino benzamide derivative. Studied N-phenyl phthalimide derivatives as
rigidified analogous amelitolide and designed the 4 amino – N- (2,6- dimethyl phthalimide) model and
subsequent phthalimide pharmacophore with out the 4 amino group the phthaliyl moiety.
Two series of phthalimides one possessing on N – phenoxy alkyl moiety substituted at position 3 or 4
of the phenyl ring the other a series of N-Alkenyl or alkenyl phthalimides. we obtained and their anticonvulsants
activity was examined.
The anticonvulsant activity of phthalimide containing an unsaturated substituent at the phthalimide nitrogen
was superior to that of the N- Phenoxy alkyl Phthalimides depends on the lengths and configuration of alkenyl
chain activity of chain length.The results obtained showed that cis configuration of the alkenyl chain was most
beneficial to activity than trans configuration.Several important variations were discovered by and his co-orkers in
the early stages of its development as a synthetic tool. This reaction is used in natural products
synthesis.Formation of a racemic phosphine oxide when a chiral phosphine (eg. Cyc-C6H11) ( - Naphthyl) in place of
(ph3p) and excess alcohol are use, indicates the involvement of analogous pentacoordinate dialkyphosporane.
PART – B
EXPERIMENTAL PROCEDURE:-
Take 1.46gm (0.1 moles) Phthalic anhydride and acetic acid in the
round bottom flask and this mixture pour in to 0.6 gm of Urea then add
porcelein piece and this reaction mixture heat on sand bath for 50 min. then
pour in to ice cold water then filtrate it and then the product are dissolved in
ethanol for recrystalized. Record practical yield and physical constant of
product.
PART B
Physical and Chemical Properties of reagents
A) Phthalic Anhydride (Apex chem.)
1) Molecular Formula = (C8H4O3)
2) Melting Point = 1300C
3) Specific Density = 1.57 gm/cm3
4) Molecular Weight = 148.12 gm/mol-1
5) PH = 2
B) Urea:-
1) Molecular Formula = CH4N2O
2) Melting Point = 1330C
3) Specific Density = 1.34 gm/cm3
4) Molecular Weight = 60.06 gm/mol-1
5) PH = 9
General Reaction
O Glacial acetic O
O
acid
O
N C NH2
Urea / heat 50 min.
O
O
phthalic anhydride
Mechanism O
- H
O
O +
O
N
.. ..
C NH2
O + H2N C NH2 O H
O O
O O
O
O
-H2O
: NH C NH2 N C NH2
OH
O
O
PHYSICAL AND CHEMICAL PROPERTIES OF PRODUCT:-
O
O
N C NH2
O
2-(Acetamide)H-isoindole-1,3(2H)-dione
Sr. No. Properties Result
1 1) IUPAC Name of the product 2-(Acetamide)H-isoindole-1,3(2H)-dione
2-(Acetamide)H-isoindole-1,3(2H)-dione
3 Molecular wt. of 190.1586
2-(Acetamide)H-isoindole-1,3(2H)-dione
4 % of yield of 9.71%
2-(Acetamide)H-isoindole-1,3(2H)-dione
5 Color of Faint pink
2-(Acetamide)H-isoindole-1,3(2H)-dione
6 Melting point of 1620 C
2-(Acetamide)H-isoindole-1,3(2H)-dione
7 IR (KBr) cm-1 of H O O
C O N
2-(Acetamide)H-isoindole-1,3(2H)-dione
H
3196cm-1, 1750-1731cm-1, 1738cm-1
IR SPECTRA OF UREA:-
PART – B
Experimental procedure:-
Take 1.46gm (0.1 moles) Phthalic anhydride and acetic acid in the
round bottom flask and this mixture pour in to 0.6 gm of Thiourea then
add porcelein piece and this reaction mixture heat on sand bath for 50
min. then pour in to ice cold water then filtrate it. And then the product
are dissolved in ethanol for recrystalized & then record yield. And
physical constant of product
PART B
Physical and Chemical Properties of reagents
A)Phthalic Unhydride (Apex chem.)
1) Molecular Formula = (C8H4O3)
2) Melting point =1300c
3) Specific Density = 1.57 gm/ cm3
4) PH=2
5) Molecular weight = 148.12gm/mol-1
B) Thiourea
1) Molecular Formula = CH4N2S
2) Specific Density = 1.405 gm/cm3
3) Molecular weight = 72.16gm/mol-1
4) PH=7
General Reaction
o Glacial acetic O
S
acid
O
Thiourea N C NH2
Heat.50 min
O
O
phthalic anhydride 2(Thiamide)-H-isoindole-1,3(2H)-dione
Mechanism
- H S
O O +
S N C NH2
.. .. H
O + H2N C NH2 O
O O
phthalic anhydride Thiourea
O
O
S S
-H2O
NH C NH2 N C NH2
OH
O O
2(Thiamide)-H-isoindole-1,3(2H)-dione
PART – A
PHYSICAL AND CHEMICAL PROPERTIES OF PRODUCT
O
S
N C 2
NH2
C
O
2(Thiamide)-H-isoindole-1,3(2H)-dione
Sr. No. Properties Result
1 IUPAC Name of the product 2(Thiamide)-H-isoindole-
1,3(2H)-dione
=1681cm-
Recrystallization of the N-substituted pthalimide
Transfer as much of the solid as possible from the Buchner
funnel to clean, dry 250ml beaker. Add 10 ml of 95% ethanol to the beaker and
if necessary, warm the mixture (does not boil).The mixture in thewater bath to
warm the mixture to dissolve the crystal. If the crystal do not all dissolve, add 2
ml more of the ethanol and continue to warm the mixture to dissolve the
crystals. complete the crystallization by placing the beaker and contain in the
ice bath (label the beaker) crystals should form. If an oil appears instead of
solid, reheat the beaker in the hot water bath until the oil disappears. If crystals
do not appear, you can scratch the bottom of beaker with a stirring rod to
reduce crystallization.
APPLICATION(USES)
1) Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and
saccharin.
2) Alkyl phthalimides are useful precursors to amines in chemical synthesis, especially in
peptide synthesis where they are used "to block both hydrogens and avoid racemization of
the substrates".
3) Alkyl halides can be converted to the N-alkylphthalimide:
C6H4(CO)2NH + RX + NaOH → C6H4(CO)2N-R + NaX + H2O
The amine is commonly liberated using hydrazine:
C6H4(CO)2NR + N2H4 → C6H4(CO)2N2H2 + RNH2
Dimethylamine can also be used
4) The most important synthesis of phthalimides is the dehydrative condensation of phthalic
anhydride at high temperatures with primary amines, when the amine is available .
5) Frequently, the term of imide refers to the combined forms such as maleimides, phthalimides, and
succinimides which are used as plastic modifiers to improve heat-resistant, antioxidant and antifoulan
properties.
6)They are used as intermediates for the synthesis of cross-linking agents, pesticides, dyes,
antiseptics and crystalline adducting agents . .
7) They are also useful compounds in the synthesis of primary amines and amino acids for the
application in the field of medicine and biological research .
8) Phthalimide, derived from phthalic anhydride with ammonium hydroxide by heating, is used in the
synthesis of primary amines and amino acids.
9) It is used to make synthetic indigo and phthalocyanine pigments which have macrocyclic structure
showing striking coloring features like porphyrins (biopigments).
RESULTS & DISCUSSION :-
-This New Synthon ‘N’ Substituted Phthalimide can be used for precursor of synthesis
of different Organic Compounds.
-N-substitued phthalimide used for synthesis of different heterocyclic
organic compounds .
REFERENCE
1. Vameeq J;Bac P;Herrenknecht ch;Maourios P;Delcourt P Stable J P med Chem.43
2. Kiec Konowiez k Zeje A.Pol J Chem.58
3. Kalo K; Mistunobu OJ Org.Chem
4. Mistunobu O Kalo, k wada M Bull Chem
5. Mistunobu O wada. M, Sano T.J Am Chemi Soc 1972
6. Kuhara T, Nakajina Y;Mistunobu, o tetrahedron
7. Kurihara T;Sygizaki, M kine, I, Wada M Mistunobu,O Bull.Chem
8. Fleming I ,Ghosh.S.K Chem, Commun 1972
9. Watatnabe,T,Grodnev.I.D.O, amoto, T. chirality 2000, 12, 346 .
10.Herb,C; Deter, F, Majer, M.E., Eur.j.org.chem. 2005, 728
Note: This service is not intended for secure transactions such as banking, social media, email, or purchasing. Use at your own risk. We assume no liability whatsoever for broken pages.
Alternative Proxies: