Gənc təDQİqatçI, 2020, VI cild, №1

 
Obtained 12.37 g (65.4%)
, 
 
МR
D
:
found - 59.75, calculated – 60.01. 
1-Phenylsulfamido- or (3-carboxypyridine)-2-hydroxybutylpropionate (XIII, XIV). Ge-
neral technique. 
0.08 mol of phenylsulfamide or nicotinic acid were dissolved in 60 ml of ethanol, 
0.09 mol of triethylamine was added. Then at stirring and 75 – 80 
0
C 0.08 mol of 1-chlorine-2-
hydroxybutylpropionate was added drop by drop. The mixture was boiled for 4-6 hours. Hot soluti-
on was filtered. 20 ml of water was added to filtrate, it was cooled, isolated crystals were filtered, 
and recrystallized from 70% of ethanol.
1-N-Phenylsulfamido-2-methyl-3-acetyl-4-diethylditiocarbomoyl-5-carboxybutylpirrol 
(XV). 
3.5 g (0.008 mol) of 1-(N,N-diethyldithiocarbamoyl)-2-phenylsulfamidobutylpropionate we-
re dissolved in 20 ml of ethanol, 1 g (0.01 mol) of acetylacetone
and 5 – 8 drops of morpholine 
were added. The mixture was boiled for 7 – 8 hours. Formed crystals were filtered, washed with 
water, dried and recrystallized from ethanol.
Table 1 shows physical and chemical properties and spectral data of the compounds I – XV.
Results and discussion 
Reaction products of chlorinesulfamidation of unsaturated compounds with chloramines have 
an important role for synthesizing N-substituted derivatives of sulfamides which are syntons for the 
synthesis of multifunctional and heterocyclic derivatives. Recently this reaction has been used for 
aminohydroxylation, aminochalcogenation, epoxydation, aziridination, allyl amination of alkenes, 
during hetarylation and so on. It is supposed that [1], the reactions with chloramines proceed with 
constants of rate 10
9 
÷ 10
10 
mol/l • sec and cause cleavage of N-Cl bond resulting in chloride ion 
and free radicals with localization of unpaired electrons on nitrogen atom. These radicals react with 
constants of rate 2·10
7
÷10
8
mol/l • sec with oxygen atoms resulting in nitrenes.

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GƏNC TƏDQİQATÇI, 2020, VI cild, №1 
40 
The reaction of unsaturated compounds with N,N-dichloramides of sulfo acids occurs fre-
quently under the effect of UV-radiation or using catalysts. Study of interaction reaction of N,N-p-
chlorbenzenesulfamide with allylchloride in ССl
4
both under the effect of UV-radiation or using 
dicyclohexylperoxidecarbonate and in their absence showed advantage of the first method [2]. 
However, together with the main products other compounds are also formed during rearrangements, 
that confirms ion-radical reaction. Maybe that’s why telomerization of acrylonitrile occurs during 
the reaction with acrylonitrile. It was shown that [3] catalytic reaction of N,N-dichlor-p-
toluenesulfamide with β-nitrilestyrene leads to aminohalogenation with high yield. Unlike them the 
reaction of N,N-dichlor-p-toluenesulfamide with alkenes in the presence of palladium results in not 
only adducts, but also aziridination [4]. Stereoselective addition of monochloramides of sulfo acids 
to unsaturated compounds proceeds with promoter СО
2 
[5] or copper (1+) catalyst [6].
Stereoselective addition occurs during the reaction of monochloramines with derivatives of al-
lyl alcohol and cis- and trans-isomers of hydroxyazipyridines are formed [7].
N-substituted sulfamides were produced during interaction of N,N-dichlor-4-chlorbenzene- or 
N,N-dichlor-4-methylbenzenesulfamides with phenylacetylene [8].
Our studies [9-11] showed that the most convenient reagents for chloramidation of unsaturat-
ed compounds are N-monochloramides of benzenesulfo acids (chloramine -B, -T, KhB and so on).
A new method of chlorination of olefins has been developed [12]. Under the effect of elec-
tron-acceptor sulfamide fragment, halides in N-2,3 position is easily substituted with nucleophiles. 
Sulfamides containing N-2,2-dichlorethyl groups with phenyldiamine form quinoxaline [13], halo-
gen in sulphonylaziridine
 
even in β-position is easily substituted resulting in benzothiazepine [14]. 
The effect of complex ether group on chloramidation reaction of acrylic ether with monochlo-
ramine – B was studied and reactivity of chlorine atom in the compounds was investigated. It was 
found that the reaction of chloramine-B with butyl ether of acrylic acid, aminly, depends on solvent 
and temperature of the reaction. During the reaction chloramidation occurs in aprotic solvent (ben-
zene, toluene): 
C
4
H
9
OOC
H
H
H
C
6
H
5
SO
2
N
Cl
Na
C
4
H
9
OOC
NHSO
2
C
6
H
5
Cl
+
(I)
HCl
This compound was used to synthesize different derivatives. Thanks to the compound (I) of 
electron-acceptor sulfamide fragment in this composition chlorine atom is easily substituted with 
nucleophiles forming 2-Z-1-phenylsulfamide-butylpropionates: 
C
4
H
9
OOC
Cl
NHSO
2
C
6
H
5
C
4
H
9
OOC
NHSO
2
C
6
H
5
ZH
z
S - C - OC
3
H
7
S
N
S
COO
C
4
H
9
NHCONH
S
NH
2
- CONH
N(C
2
H
5
)
2
C
6
H
5
CH
2
NH
Z = -SCN(C
2
H
5
)
2
S
(II); 
(III); CNS (IV); 
_
(V);
(VI);
(VII) ;
(VIII);
(IX);
(X)

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KIMYA 
ELMLƏRİ
 
41 
During the reaction of chloramine with butylacrylate in aqueous solution chlorohydrine is 
formed, in the presence of alcohol chlorether of butylacrylate is obtained: 
C
4
H
9
OOC
H
H
H
C
6
H
5
SO
2
N
Cl
Na
ROH
C
4
H
9
OOC
OR
Cl
R = OH
C
4
H
9
+
+
HCl
(XI);
(XII)
Probably, the reaction goes with formation of hypochlorite. 
Compounds XI and XII are syntons for the synthesis of multifunctional compounds. N-
alkylation occurs during interaction of chlorhydrine XI with benzenesulfanylamide in the presence 
of pyridine: 
C
6
H
5
SO
2
NH
2
Cl
COOC
4
H
9
OH
C
6
H
5
SO
2
NH
COOC
4
H
9
OH
+
(XIII)
During the reaction with nicotinic acid compound XI forms nicotinic acid that confirms high 
mobility of chlorine atom: 
COOC
4
H
9
OH
Cl
N
N
COOH
COO
OH
COOC
4
H
9
+
(XIV)
Synthesized derivatives of butyl ether of acrylic acid are dipolar compounds, that’s why there 
is 1,3-dipolar addition to 
polarophiles. 
Multifunctional compounds II – XIV are syntons for the 
synthesis of heterocyclic compounds.
Despite sterically hindered structure the compound II with acetylacetone forms N-
phenylsulfamide-2,4-dimethyl-5-N,N-diethyldithiocarbamoylpyrrol:
SCN(C
2
H
5
)
S
C
4
H
9
OOC
NHSO
2
C
6
H
7
O
O
CH
3
CH
3
(C
2
H
5
)
2
N - C - S
S
CH
3
SO
2
C
6
H
5
COOC
4
H
9
N
COCH
3
+
(XV)
The formation of the compound (XV) proves that synthesized compounds may be synthons 
for heterocyclic compounds 
Preliminary researches of synthesized compounds showed their high antimicrobial properties. 
Thus, using monochloramine as a key reagent it is possible to synthesize multifunctional sul-
famide compounds which are 1,3- dipolarophils. Therefore they, in turn, are synthons for synthesis 
of various heterocyclic compounds. Furthermore, by the reaction of chloramine with butyl acrylate, 
it is possible to easily synthesize compounds with various functional groups that are difficult or im-
possible to obtain in another way. 

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GƏNC TƏDQİQATÇI, 2020, VI cild, №1 
42