Synthesis of 2-phthalimidoethanesulfonic acid imidazolides

Full text of DOI:10.1134/S1070428013060250

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2013, Vol. 49, No. 6, pp. 934–935. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © T.S. Yudakhina, Yu.V. Moreva, Yu.P. Zarubin, P.P. Purygin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49,
No. 6, pp. 947–948.
SHORT
COMMUNICATIONS
Synthesis of 2-Phthalimidoethanesulfonic Acid Imidazolides
T. S. Yudakhina, Yu. V. Moreva, Yu. P. Zarubin, and P. P. Purygin
Samara State University, ul. Akad. Pavlova 1, Samara, 443011 Russia
e-mail: utschem-2007@mail.ru
Received November 10, 2012
DOI: 10.1134/S1070428013060250
2-Aminoethanesulfonic acid (I) is known to exhibit
a broad spectrum of biological activity [1–3]. Hetero-
cyclic amides derived from organic and inorganic acids
(azolides) are widely used in various fields of medicine
and industry as antibacterial agents, pesticides, fungi-
cides, herbicides, monoamine oxidase inhibitors, and
pharmacophores for antihelminthic agents and anal-
gesics [4].
silylimidazole IVa–IVe was added, and the mixture
was stirred at room temperature, the progress of the
reaction being monitored by TLC. Evaporation of the
mixture gave compound Va–Ve as a colorless or light
yellow solid.
2-[2-(1H-Imidazol-1-ylsulfonyl)ethyl]-2,3-dihy-
dro-1H-isoindole-1,3-dione (Va). Reaction time 1.5 h.
Yield 1.02 g (91%), mp 128–130°C, Rf 0.25. IR spec-
trum, ν, cm−1: 1783 (C=O), 1333 (SO2), 905 (S–N).
1H NMR spectrum, δ, ppm: 3.40 t (2H, CH2SO2),
4.55 t (2H, CH2N), 7.26 d (1H, 5′-H), 7.67 d (1H,
4′-H), 8.11 s (1H, 2′-H). Found, %: C 51.20; H 3.58;
N 13.69; S 10.51. C13H11N3O4S. Calculated, %:
C 51.15; H 3.61; N 13.77; S 10.49.
Taking the above stated into account we have syn-
thesized previously unknown 2-phthalimidoethanesul-
fonic acid imidazolides Va–Ve and examined their
physicochemical characteristics.
Sodium 2-phthalimidoethanesulfonate (II),
2-phthalimidoethanesulfonyl chloride (III), and
N-trimethylsilylimidazoles IVa–IVe were synthesized
according to the procedures described in [5–7].
2-[2-(2-Methyl-1H-imidazol-1-ylsulfonyl)ethyl]-
2,3-dihydro-1H-isoindole-1,3-dione (Vb). Reaction
time 6 h. Yield 0.87 g (76%), mp 119–120°C, Rf 0.20.
IR spectrum, ν, cm−1: 1779 (C=O), 1330 (SO2), 902
2-Phthalimidoethanesulfonic acid imidazolides
Va–Ve (general procedure). 2-Phthalimidoethanesul-
fonyl chloride (III), 1.0 g (0.0037 mol), was dissolved
in 10 ml of chloroform, 0.0037 mol of N-trimethyl-
1
(S–N). H NMR spectrum, δ, ppm: 2.45 s (3H,
2′-CH3), 3.68 t (2H, CH2SO2), 4.42 t (2H, CH2N),
O
O
(1) AcONa
(2) Phthalic anhydride
SO3 Na+
SO2Cl
SOCl2
SO3
N
N
H3N
O
O
I
II
III
O
N
SO2Ht
HtSiMe3 (IVa–IVe)
O
Va–Ve
Ht = 1H-imidazol-1-yl (a), 2-methyl-1H-imidazol-1-yl (b), 2-isopropyl-1H-imidazol-1-yl (c), 4-methyl-1H-imidazol-1-yl (d),
1H-benzimidazol-1-yl (e).
934

SYNTHESIS OF 2-PHTHALIMIDOETHANESULFONIC ACID IMIDAZOLIDES
935
7.18 d (1H, 5′-H), 7.76 d (1H, 4′-H). Found, %:
C 52.58; H 3.97; N 13.23; S 9.97. C14H13N3O4S. Cal-
culated, %: C 52.66; H 4.08; N 13.17; S 10.03.
N 12.07; S 9.12. C17H13N3O4S. Calculated, %:
C 57.46; H 3.66; N 11.83; S 9.02.
Thin-layer chromatography was performed on
Kieselgel 60 F254 plates (Merck, Germany) using
methylene chloride–acetone (10:1) as eluent; spots
were visualized under UV light (using a Khromato-
skop M ultrachemiscope, λ 254 nm) and by treatment
with iodine vapor.
2-[2-(2-Isopropyl-1H-imidazol-1-ylsulfonyl)-
ethyl]-2,3-dihydro-1H-isoindole-1,3-dione (Vc). Re-
action time 8 h. Yield 0.93 g (73%), mp 113–115°C,
Rf 0.18. IR spectrum, ν, cm−1: 1781 (C=O), 1335
1
(SO2), 907 (S–N). H NMR spectrum, δ, ppm: 1.33 d
(6H, CH3), 3.56 m (1H, 2′-CH), 4.07 t (2H, CH2SO2),
4.36 t (2H, CH2N), 7.08 d (1H, 5′-H), 7.69 d (1H,
4′-H). Found, %: C 55.38; H 4.92; N 12.26; S 9.10.
C16H17N3O4S. Calculated, %: C 55.33; H 4.90;
N 12.11; S 9.22.
The IR spectra were recorded in KBr on a Perkin
Elmer Spectrum 100 spectrometer (USA) with Fourier
transform. The H NMR spectra were measured on
a Bruker AM 300 instrument (FRG) at 300 MHz using
DMSO-d6 as solvent.
1
2-[2-(4-Methyl-1H-imidazol-1-ylsulfonyl)ethyl]-
2,3-dihydro-1H-isoindole-1,3-dione (Vd). Reaction
time 3 h. Yield 0.98 g (84%), mp 123–125°C, Rf 0.23.
IR spectrum, ν, cm−1: 1784 (C=O), 1338 (SO2), 909
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(S–N). H NMR spectrum, δ, ppm: 2.26 s (3H,
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dihydro-1H-isoindole-1,3-dione (Ve). Reaction time
5 h. Yield 1.13 g (87%), mp 133–135°C, Rf 0.23.
IR spectrum, ν, cm−1: 1785 (C=O), 1337 (SO2), 908
1
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 6 2013