Preparation of 3,3-bis(ethylthiol)-2-arylacrylonitrile and 3,3-bis(ethoxyacetatethiol)-2-arylacrylonitrile via an electrogenerated base-promoted reaction

Article abstract of DOI:10.1080/17415993.2012.705285

A simple method for the preparation of 3,3-bis(ethylthiol)-2- arylacrylonitrile and 3,3-bis(ethoxyacetatethiol)-2-arylacrylonitrile is described. The electrogenerated cyanomethyl base/anion obtained from electroreduction of acetonitrile promotes reactions between an arylacetonitrile, carbon disulfide and ethyl iodide or ethyl 2-chloroacetate. The products are obtained in good yields under mild reaction conditions with respect to previously reported methods. The effect of the number of Faradays and mechanism of the reaction are discussed.

Full text of DOI:10.1080/17415993.2012.705285

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Preparation of 3,3-bis(ethylthiol)-2-
arylacrylonitrile and 3,3-
bis(ethoxyacetatethiol)-2-
arylacrylonitrile via an
electrogenerated base-promoted
reaction
Taieb Saied a b , Noureddine Raouafi b & Khaled Boujlel b
a Département de Chimie et de Biologie Appliquées, Institut
National des Sciences Appliquées et de Technologie, B.P. 676,
1080, Tunis Cedex, Tunisie
b Laboratoire de Chimie Analytique et Electrochimie, Faculté des
Sciences de Tunis, Université Tunis El-Manar, Campus Universitaire,
2092, Tunis, Tunisia
Published online: 10 Aug 2012.
To cite this article: Taieb Saied , Noureddine Raouafi & Khaled Boujlel (2012) Preparation of
3,3-bis(ethylthiol)-2-arylacrylonitrile and 3,3-bis(ethoxyacetatethiol)-2-arylacrylonitrile via
an electrogenerated base-promoted reaction, Journal of Sulfur Chemistry, 33:5, 513-520, DOI:
10.1080/17415993.2012.705285
To link to this article: http://dx.doi.org/10.1080/17415993.2012.705285
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Journal of Sulfur Chemistry
Vol. 33, No. 5, October 2012, 513–520
Preparation of 3,3-bis(ethylthiol)-2-arylacrylonitrile and
3,3-bis(ethoxyacetatethiol)-2-arylacrylonitrile via an
electrogenerated base-promoted reaction
Taieb Saieda,b*, Noureddine Raouafib and Khaled Boujlelb
aDépartement de Chimie et de Biologie Appliquées, Institut National des Sciences Appliquées et de Tech-
nologie, B.P. 676, 1080 Tunis Cedex, Tunisie; bLaboratoire de Chimie Analytique et Electrochimie, Faculté
des Sciences de Tunis, Université Tunis El-Manar, Campus Universitaire 2092 Tunis, Tunisia
(Received 17 May 2012; final version received 19 June 2012)
Asimplemethodforthepreparationof3,3-bis(ethylthiol)-2-arylacrylonitrileand3,3-bis(ethoxyacetatethiol)-
2-arylacrylonitrile is described. The electrogenerated cyanomethyl base/anion obtained from electroreduc-
tion of acetonitrile promotes reactions between an arylacetonitrile, carbon disulfide and ethyl iodide or
ethyl 2-chloroacetate. The products are obtained in good yields under mild reaction conditions with respect
to previously reported methods. The effect of the number of Faradays and mechanism of the reaction are
discussed.
Keywords: 3,3-bis(ethylthiol)-2-arylacrylonitrile; 3,3-bis(ethoxyacetatethiol)-2-arylacrylonitrile; carbon
disulfide; arylacetonitrile; electrogenerated base
Introduction
Thanks to their prominence in the synthesis of several biologically active molecules, such as
fungicidals, flavonoid pigments, and sexual pheromones, numerous studies have been devoted
to the exploration of the reactivity of arylacetonitriles (1–5). However, in order to avoid the use
of polluting solvents and to circumvent the difficulties of the experimental protocols involved in
*Corresponding author. Email: saied.taieb@gmail.com
ISSN 1741-5993 print/ISSN 1741-6000 online
© 2012 Taylor & Francis
http://dx.doi.org/10.1080/17415993.2012.705285
http://www.tandfonline.com

514 T. Saied et al.
classic syntheses, new approaches under very mild conditions are needed. In the literature, the
condensations of arylacetonitriles with carbonyls, isothiocyanates, and 1,2 – and 1,3 – dihalo-
genated alkanes are based on the traditional Knovenagel reaction which use strongly basic alkalai
hydroxides or hydrides (6). Recently, it was found these bases could be substituted by elec-
trogenerated bases (EGBs) to promote reactions sometimes in higher yields and under milder
conditions (7–9). Electrogenerated species-promoted reactions in general proceed smoothly with
an easy work-up and do not require harsh reaction conditions such as high temperatures or the
use of highly reactive reagents. EGBs were initially mentioned by Baizer and coworkers (10)
and recently used by Feroci et al. (11–16) for the preparation of carbonates, carbamates and
oxazolines in two compartments cell.
In the past few years, we have focused on the development of an alternative synthesis
of acyclic dithiocarbamates, N-benzylic rhodanines, and thiazolidine-2-thiones, respectively,
from primary and secondary aliphatic and benzylic amines, carbons disulfide, alkyl halides,
2-bromoacetate and 2-chloroacetone using in situ EGBs (7–9). To the best of our knowledge,
no electrochemical method has been published to date on the reaction between arylacetoni-
trile and electrogenerated species. Hence, the aim of this study is to develop the reactivity of
these compounds by using EGBs. The study reports the electrochemical promoted synthesis of
3,3-bis(ethylthiol)-2-arylacrylonitrile (2) and 3,3-bis(ethoxyacetatethiol)-2-arylacrylonitrile (3)
starting from arylacetonitrile (Scheme 1) A series of compounds were prepared and the effect of
the number of Faradays and the mechanism are discussed.
Scheme 1. Synthesized products (2) and (3) from arylacetonitrile via EGB-assisted reaction.
Results and discussion
Cyclic voltammetry of arylacetonitrile (1) in tetrabutylammonium tetrafluoroborate acetonitrile
solution (0.1 mol/L) on a platinum electrode show that arylacetonitriles are not appreciably
electroactive and are not reduced which means that they can be introduced either in the begin-
ning (method A) or at the end of the electrolysis (method B) according to Feroci et al. (17)
procedure.
Electrolysis at constant current density in the presence of tetrabutylammonium tetrafluoroborate
(0.1 mol/L) as the supporting electrolyte, in an undivided cell cooled at −20 ◦C fitted with a
magnesium rod as the anode and a stainless steel grid cathode, under an inert atmosphere of
nitrogen, probably yields the arylacetonitrile with the cyanomethyl carbanions. The electrolysis
is stopped approximately after 3–4 h of reaction. This time is enough to permit the formation of
5 × 10−3 mole of EGB. Then, carbon disulfide is added immediately to the solution followed by
ethyl iodide or ethyl-2-chloroacetate 15 min later. The mixture is continually stirred over night at
ambient temperature. The products are isolated following standard work-up procedure (6–8) and
purified by column chromatography. All the resulting products reported in Table 1 were identified
by examination of their spectroscopic data.

Journal of Sulfur Chemistry 515
Table 1. Synthesized 3,3-bis(ethylthiol)-2-arylacrylonitrile (2) and 3,3-bis(ethoxyacetatethiol)-2-arylacrylonitrile (3).
Entry
Starting arylacetonitrile
Electrophile
Product
Qa
Yieldb (%)
1
A
2
71
2
3
A
A
2
2
75
76
4
5
A
A
2
2
69
65
6
B
2
62
7
8
B
B
2
2
60
59
(Continued).

516 T. Saied et al.
Table 1. Continued.
Entry
Starting arylacetonitrile
Electrophile
Product
Qa
Yieldb (%)
9
B
2
68
10
B
2
73
Notes: A, ethyliodide; B, ethyl 2-chloroacetate. aThe consumed quantity of electricity represents the number of Faradays per mole of
arylacetonitrile. bThe yield was calculated in regard to the starting arylacetonitrile.
The EGB is presumed to be, in the present case, primarily the cyanomethyl carbanion, formed
along with dihydrogen by the reduction of acetonitrile (7–9) at the stainless steel grid cathode
and stabilized with the electrogenerated Mg2+ cations formed by oxidation of the sacrificial
magnesium anode. The EGB deprotonates the arylacetonitrile to yield a second anion that reacts
with CS2 to yield the corresponding Mg dithiocarbonic salt (I).
Scheme 2. Proposed mechanism of the preparation of products (2) and (3) by EGB-promoted
reaction.
The intermediate anion (I) probably tautomerizes to give anion (II) that is preferentially stabi-
lized by conjugation. A second EGB removes the mobile proton of the –SH group to yield the
dianions. Finally, alkylation by two equivalents of ethyl iodide or ethyl 2-chloroacetate yields the
products (2) and (3), respectively.
Phenylacetonitrile is chosen as the standard starting reagent in order to study the effect of the
number of Faradays on the reaction yield (Table 2). It was found that the yield increases as the
number of Faradays increases to reach a satisfactory yield of 76% at ca. 2 Faraday. When the
number of Faraday is ca. 5 the yield is improved only by 10%. So, 2.0–2.5 Faraday seems a good
compromise between a good yield of the reaction and the current consumption. Moreover, at 5
Faraday a byproduct (4) yield, formed by the autocondensation reaction of acetonitrile, increases
dramatically (Scheme 3) (8).

Journal of Sulfur Chemistry 517
Scheme 3. Preparation of byproduct (4) by reaction of autocondensation of acetonitrile.
Table 2. Variation of the yield of 2c as a function of the consumed number of
Faradays in respect to the amount of arylacetonitrile.
Entry
Q/F (mol−1
)
Yield of 2c (%)
Time (min)
1
2
3
4
5
1
2
3
4
5
56
76
82
85
86
100
200
300
400
500
The amount of acetonitrile is reduced by evaporation and the resulting mixture was extracted
three times with 50 ml ether. The ethereal phase was washed by small amounts of water and
dried over magnesium sulfate. The ether was removed and the residue was purified by column
=
chromatography on silica gel 60 using ethyl acetate/petrol ether (v:v 1:9) as eluent. Products
(2) and (3) were identified by IR, NMR spectroscopy, GC–MS and elemental analysis.
Conclusion
In conclusion, the use of an EGB provides a new electrochemical methodology that
allows the preparation of 3,3-bis(ethylthiol)-2-arylacrylonitriles and 3,3-bis(ethoxyacetatethiol)-
2-arylacrylonitrile (3) from arylacetonitrile, carbon disulfide and ethyliodide or ethyl-2-
chloroacetate in high yields. The reaction occurs under mild conditions and avoids the use of
polluting or hazardous chemicals or the addition of a base. The mechanism of the reaction is
investigated by cyclic voltammetry and the effects of number of Faradays on the reaction yield
have been studied.
Experimental
3,3-bis(ethylthio)-2-phenylacrylonitrile (2a)
1
Yield: 71%: IR (cm−1, CHCl3)ν: 2220 (CN); 1600 (C C). H NMR (300 MHz, CDCl3) δ: 1.10
=
(t, 3H, CH3); 1.25 (t, 3H, CH3); 2.60 (q, 2H, CH2); 2.90 (q, 2H, CH2); 7.20–7.40 ( mu, 4H, CH
arom.). 13C NMR (75.47 MHz, CDCl3) δ: 13.65; 13.76; 28.31; 29.06; 114.38; 117.41; 126.04;
126.33; 126.46; 126.87; 127.26; 127.80; 133.19; 153.50. MS (EI) m/z: 77 (10); 89 (16); 105
(30); 115 (15); 133 (20); 159 (100); 160 (45); 192 (25); 220 (12); 249 (80). Elemental analysis:
=
=
=
=
=
=
%C /60.01; %H 5.82; %N 5.40 (experimental). %C 62.61; %H 6.06; %N 5.62
(calculated).
3,3-bis(ethylthio)-2-(4-fluorophenyl)acrylonitrile (2b)
Yield: 75%: IR (cm−1, CHCl3)ν: 2226 (CN); 1608 (C C). H NMR (300 MHz, CDCl3) δ: 1.20
1
=
(t, 3H, CH3); 1.30 (t, 3H, CH3); 2.75 (q, 2H, CH2); 2.95 (q, 2H, CH2); 6.90–7.40 (mu, 4H, CH

518 T. Saied et al.
arom.). 13C NMR (75.47 MHz, CDCl3) δ: 14.69; 14.76; 29.82; 30.14; 115.51; 117.22; 128.42;
129.31; 129.55; 129.72; 130.25; 131.28; 154.88; 160.89. 19F NMR (282.37 MHz, CDCl3) δ:
−110.23 (s, 1F, CF arom.). MS (EI) m/z: 61 (10); 105 (24); 133 (32); 151 (20); 177 (100); 178
=
=
=
(40), 210 (30); 238 (11); 267.1 (80). Elemental analysis: %C /60.53; %H 5.46; %N 5.62
=
=
=
(experimental). %C 58.39; %H 5.28; %N 5.24 (calculated).
3,3-bis(ethylthio)-2-(p-tolyl)acrylonitrile (2c)
1
Yield: 76%: IR (cm−1, CHCl3)ν: 2222 (CN); 1608 (C C). H NMR (300 MHz, CDCl3) δ: 1.20 (t,
=
3H, CH3); 1.40 (t, 3H, CH3); 2.40 (s, 3H, CH3); 2.75 (q, 2H, CH2); 3.10 (q, 2H, CH2); 7.20–7.40
(mu, 4H, CH arom.). 13C NMR (75.47 MHz, CDCl3) δ: 14.75; 14.67; 21.33; 29.25; 30.07; 115.80;
118.50; 128.55; 128.66; 129.08; 129.21; 129.67; 129.72; 138.92; 153.44. MS (EI) m/z: 91.1 (20);
119.1 (18); 148.0 (14.5); 172.0 (38); 173.0 (100); 174.0 (34.5); 206.0 (16); 234.0 (11); 263.1
=
=
=
=
(80). Elemental analysis: %C /59.93; %H 6.34; %N 5.88 (experimental). %C 63.83;
=
=
%H 6.50; %N 5.32 (calculated).
3,3-bis(ethylthio)-2-(4-methoxyphenyl)acrylonitrile (2d)
1
Yield: 69%: IR (cm−1, CHCl3)ν: 2221 (CN); 1606 (C C). H NMR (300 MHz, CDCl3) δ: 1.15 (t,
3H, CH3); 1.30 (t, 3H, CH3); 2.70 (q, 2H, CH2); 2.90 (q, 2H, CH2); 3.70 (s, 3H, CH3); 6.80–7.35
(mu, 4H, CH arom.). 13C NMR (75.47 MHz, CDCl3) δ: 14.71; 14.72; 29.32; 29.66; 55.22; 113.42;
113.91; 114.54; 126.56; 126.60; 129.05; 129.77; 152.47; 159.85. MS (EI) m/z: 69 (10); 102 (11);
=
=
146 (24); 167 (30); 189.0 (100); 199 (20) 250 (10); 279.1 (49). Elemental analysis: %C /61.33;
=
=
=
=
=
%H 5.98; %N 5.26 (experimental). %C 60.18; %H 6.13; %N 5.01 (calculated).
3,3-bis(ethylthio)-2-(2-methoxyphenyl)acrylonitrile (2e)
1
Yield: 65%: IR (cm−1, CHCl3)ν: 2227 (CN); 1602 (C C). H NMR (300 MHz, CDCl3) δ: 1.25
=
(t, 3H, CH3); 1.45 (t, 3H, CH3); 2.70 (q, 2H, CH2); 3.00 (q, 2H, CH2); 3.8 (s, 3H, CH3); 7.20
–7.40 (mu, 4H, CH arom.). 13C NMR (75.47 MHz, CDCl3) δ: 14.75; 14.77; 28.88; 29.71; 55.54;
110.54; 111.76; 117.50; 126.50; 126.60; 129.06; 129.17; 155.54; 156.78. MS (EI) m/z: 146
=
=
(25); 174 (28); 189.0 (100); 250 (10); 279 (50). Elemental analysis: %C /60.72; %H 6.04;
=
=
=
=
%N 5.39 (experimental). %C 60.18; %H 6.13; %N 5.01 (calculated).
3,3-bis(ethoxyacetatethiol)-2-phenylacrylonitrile (3a)
1
Yield: 62%: IR (cm−1, CHCl3)ν: 2225 (CN); 1730 (C O); 1604 (C C). H NMR (300 MHz,
CDCl3) δ: 1.10 (t, 3H, CH3); 1.20 (t, 3H, CH3); 3.50 (s, 2H, CH2); 3.70 (s, 2H, CH2); 4.10 (q,
2H, CH2); 4.20 (q, 2H, CH2); 7.30–7.40 (mu, 5H, CH arom.). 13C NMR (75.47 MHz, CDCl3) δ:
14.00; 14.05; 36.31; 36.60; 61.97; 62.04; 117.53; 119.32; 128.12; 128.29; 128.71; 128.91; 129.06;
133.51; 151.32; 168.09; 168.25. MS (EI) m/z: 77 (13); 115 (27); 159 (100); 160 (50); 204 (100);
=
=
=
=
=
205 (40); 232 (19); 278 (43); 365.1 (48). Elemental analysis: %C /56.15; %H 5.37; %N 3.76
=
=
=
(experimental). %C 55.87; %H 5.24; %N 3.83 (calculated).
3,3-bis(ethoxyacetatethiol)-2-(4-fluorophenyl)acrylonitrile (3b)
1
Yield: 60%: IR (cm−1, CHCl3)ν: 2225 (CN); 1731 (C O); 1605 (C C). H NMR (300 MHz,
=
=
CDCl3) δ: 1.30 (t, 3H, CH3); 1.40 (t, 3H, CH3); 3.60 (s, 2H, CH2); 3.80 (s, 2H, CH2); 4.20 (q,

Journal of Sulfur Chemistry 519
2H, CH2); 4.30 (q, 2H, CH2); 7.10–7.60 (mu, 4H, CH arom.). 13C NMR (75.47 MHz, CDCl3) δ:
14.08; 14.11; 36.31; 36.80; 62.10; 62.13; 115.77; 116.06; 117.47; 118.46; 129.52; 129.56; 131.24;
131.35; 151.61; 168.09; 168.20. 19F NMR (282.37 MHz, CDCl3) δ: −110.24 (s, 1F, CF arom.).
MS (EI) m/z: 61 (10); 105 (24); 133 (32); 151 (20); 177 (100); 178 (40), 222 (100); 223 (51)
=
=
=
238 (11); 383.1 (50). Elemental analysis: %C /54.53; %H 5.07; %N 3.87 (experimental).
=
=
=
%C 53.25; %H 4.73; %N 3.65 (calculated).
3,3-bis(ethoxyacetatethiol)-2-(p-tolyl)acrylonitrile (3c)
Yield: 59%: IR (cm−1, CHCl3)ν: 2223 (CN); 1735 (C O); 1606 (C C). H NMR (300 MHz,
CDCl3) δ: 1.30 (t, 3H, CH3); 1.40 (t, 3H, CH3); 2.40 (s, 3H, CH3); 3.60 (s, 2H, CH2); 3.80 (s,
2H, CH2); 4.20 (q, 2H, CH2); 4.30 (q, 2H, CH2); 7.20–7.40 (mu, 4H, CH arom.). 13C NMR
(75.47 MHz, CDCl3) δ: 14.60; 14.69; 23.22; 36.25; 36.87; 62.50; 62.53; 114.65; 118.65; 127.36;
128.36; 129.51; 129.60; 131.52; 135.63; 151.44; 167.96; 168.09. MS (EI) m/z: 91.1 (25); 119.1
(11); 172.0 (45); 173.0 (100); 174.0 (36); 206.0 (16); 218 (100); 219 (49); 379.1 (40). Elemen-
1
=
=
=
=
=
=
=
tal analysis: %C /56.03; %H 5.16; %N 3.40 (experimental). %C 56.97; %H 5.58;
=
%N 3.69 (calculated).
3,3-bis(ethoxyacetatethiol)-2-(4-methoxyphenyl)acrylonitrile (3d)
1
Yield: 68%: IR (cm−1, CHCl3)ν: 2226 (CN); 1736 (C O); 1606 (C C). H NMR (300 MHz,
CDCl3) δ: 1.20 (t, 3H, CH3); 1.30 (t, 3H, CH3); 3.60 (s, 2H, CH2); 3.80 (s, 2H, CH2); 3.90 (s,
3H, CH3); 4.20 (q, 2H, CH2); 4.30 (q, 2H, CH2); 7.00–7.50 (mu, 4H, CH arom.). 13C NMR
(75.47 MHz, CDCl3) δ: 14.07; 14.10; 36.32; 36.80; 55.37; 61.98; 62.03; 114.07; 115.03; 117.75;
119.54; 125.75; 128.82; 130.65; 149.00; 160.34; 168.19; 168.33. MS (EI) m/z: 102 (15); 146 (29);
=
=
=
167 (30); 189.0 (100); 199 (20); 234 (100); 235 (56); 395.1 (45). Elemental analysis: %C /55.10;
=
=
=
=
=
%H 5.67; %N 3.82 (experimental). %C 54.66; %H 5.35; %N 3.54 (calculated).
3,3-bis(ethoxyacetatethiol)-2-(2-methoxyphenyl)acrylonitrile (3e)
Yield: 73%: IR (cm−1, CHCl3)ν: 2224 (CN); 1735 (C O); 1603 (C C). H NMR (300 MHz,
CDCl3) δ: 1.20 (t, 3H, CH3); 1.30 (t, 3H, CH3); 3.60 (s, 2H, CH2); 3.80 (s, 2H, CH2); 3.90 (s,
3H, CH3); 4.20 (q, 2H, CH2); 4.30 (q, 2H, CH2); 7.00–7.20 (mu, 4H, CH arom.). 13C NMR
(75.47 MHz, CDCl3) δ: 14.10; 14.12; 36.45; 36.91; 54.97; 62.08; 62.15; 114.25; 115.17; 118.05;
119.61; 125.60; 128.92; 131.05; 148.89; 159.43; 168.21; 168.30. MS (EI) m/z: 102 (18); 146 (30);
1
=
=
=
167 (41); 189.0 (100); 199 (20); 234 (100); 235 (49); 395.1 (50). Elemental analysis: %C /54.22;
=
=
=
=
=
%H 5.62; %N 3.73 (experimental). %C 54.66; %H 5.35; %N 3.54 (calculated).
3-amino-2-cyanobut-2-enedithioate ethyl (4a)
1
IR (cm−1, CHCl3)ν: 3330 (NH2); 2189 (CN); 1600 (C C); 1192 (C S). H NMR (300 MHz,
CDCl3) δ: 1.30 (t, 3H, CH3); 2.40 (s, 3H, CH3); 3.2 (q, 2H, CH2); 6.5 (s, 2H, NH2). 13C NMR
(75.47 MHz, CDCl3) δ: 12.02; 24.55; 29.01; 93.66; 118.25; 167.17; 212.02.
=
=
2-((3-amino-2-cyanobut-2-enethioyl)thio) acetate ethyl (4b)
1
IR (cm−1, CHCl3)ν: 3334 (NH2); 2193 (CN); 1734 (C O); 1606 (C C); 1201 (C S). H NMR
=
=
=
(300 MHz, CDCl3) δ: 1.29 (t, 3H, CH3); 2.20 (s, 3H, CH3); 3.80 (s, H, CH); 4.10 (q, 2H, CH2)

520 T. Saied et al.
8.60 (s, 2H, NH2). 13C NMR (75.47 MHz, CDCl3) δ: 14.10; 23.34; 39.50; 61.01; 69.22; 115.06;
168.62; 174.66; 220.02.
Acknowledgements
The authors gratefully acknowledge the Tunisian “Ministère de l’Enseignement Supérieur, de la Recherche et la
Technologie” for financial support (Lab. CH-02).
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