Synthesis of 2-(4-tolyloxyacetylamido)-5-aryloxymethyl-1,3,4-thiadiazoles under microwave irradiation

Article abstract of DOI:10.1081/SCC-100000174

2-(4-Tolyloxyacetylamido)-5-aryloxymethyl-1,3,4-thiadiazoles (IIa-j) are synthesized under microwave irradiation by the cyclization of 1-aryloxyacetyl-4-(4-tolyloxyacetyl)-thiosemicarbazides (Ia-j) in the presence of glacial acetic acid.

Full text of DOI:10.1081/SCC-100000174

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SYNTHESIS OF 2-(4-TOLYLOXYACETYLAMIDO)-5-
ARYLOXYMETHYL-1,3,4-THIADIAZOLES UNDER
MICROWAVE IRRADIATION
Xicun Wang a , Zheng Li b & Yuxia Da a
a Department of Chemistry, Northwest Normal University, Lanzhou, Gansu, 730070, P.R.
China
b Department of Chemistry, Northwest Normal University, Lanzhou, Gansu, 730070, P.R.
China
Published online: 09 Nov 2006.
To cite this article: Xicun Wang , Zheng Li & Yuxia Da (2001) SYNTHESIS OF 2-(4-TOLYLOXYACETYLAMIDO)-5-
ARYLOXYMETHYL-1,3,4-THIADIAZOLES UNDER MICROWAVE IRRADIATION, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 31:1, 19-26, DOI: 10.1081/SCC-100000174
To link to this article: http://dx.doi.org/10.1081/SCC-100000174
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SYNTHETIC COMMUNICATIONS, 31(1), 19–26 (2001)
SYNTHESIS OF
2-(4-TOLYLOXYACETYLAMIDO)-5-
ARYLOXYMETHYL-1,3,4-THIADIAZOLES
UNDER MICROWAVE IRRADIATION
Xicun Wang, Zheng Li,∗ and Yuxia Da
Department of Chemistry, Northwest Normal University,
Lanzhou, Gansu, 730070, P.R. China
ABSTRACT
2-(4-Tolyloxyacetylamido)-5-aryloxymethyl-1,3,4-thiadia-
zoles (IIa–j) are synthesized under microwave irradiation by the
cyclization of 1-aryloxyacetyl-4-(4-tolyloxyacetyl)-thiosemicar-
bazides (Ia–j) in the presence of glacial acetic acid.
Aryloxyacetic acid derivatives have been used as herbicides (1), diuretics
(2), and plant-growth regulators (3–5). Meanwhile, substituted 1,3,4-thiadiazoles
have also attracted much attention due to their diverse biological activities, such
as antimicrobial (6–11), antibacterial (12), anesthetic (13), antithrombotic (14),
anticonvulsant(15), cardiotonic(16), antihypertensive(17), antiinflammatory(18),
and antiulcer (19) activity.
Keeping in view the above facts, we report herein the preparation of a new
series of compounds bearing both 1,3,4-thiadiazole and aryloxyacetyl moiety, with
the objective of obtaining new biologically active compounds.
∗ To whom correspondence should be addressed.
19
Copyright ꢀ 2001 by Marcel Dekker, Inc.
www.dekker.com
C

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WANG, LI, AND DA
Scheme
Although the substituted 1,3,4-thiadiazoles can be prepared from the sub-
stituted thiosemicarbazides by conventional method (20,21), the reaction yield is
often not high and the reaction time is always very long. This paper introduces a
convenient and efficient microwave method.
Reaction of 4-tolyloxyacetyl chloride with ammonium thiocyanate catalyzed
by polyethylene glycol-400 (PEG-400) at room temperature gives 4-tolyloxyacetyl
isothiocyanate, which, on treatment with aryloxyacetic acid hydrazides in situ
at room temperature, affords 1-aryloxyacetyl-4-(4-tolyloxyacetyl)-thiosemicar-
bazides (Ia–j) in excellent yields. Compounds (Ia–j) on exposure to microwave
irradiation in the presence of glacial acetic acid result in the formation of 2-(4-
tolyloxyacetylamido)-5-aryloxymethyl-1,3,4-thiadiazoles (IIa–j) (Scheme).
The characterization of compounds Ia–j and IIa–j is based on their IR
1
(KBr), H NMR and elemental analyses. The IR spectra exhibit a characteristic
strong absorption at 1185–1195 cm−1 for compounds Ia–j attributable to the C S
==
of the thio residue. The carbonyl absorption is observed at 1708–1718 cm−1 for
1
Ia–j and 1697–1717 cm−1 for IIa–j. The H NMR spectral data of Ia–j in d6-
dimethylsulfoxide show peaks at 12.68–12.85 (NHa), 10.03–10.66 (NHb), 9.38–
9.60 (NHc) and 4.62–4.76 ppm (CH2). In contrast, the 1H NMR spectral data of
IIa–j in the same deuterated solvent show signals at 12.87–13.03 (NH), indicating
a significant downfield shift (ca. 0.2 ppm), compared to the corresponding NHa
of Ia–j, and two singlet at 5.58–5.71, 4.70–4.91 ppm (CH2), although only one
singlet for two CH2 in the Ia–j, indicating the obviously environmental changes
of CH2 in the IIa–j, in comparison with Ia–j. All found of C, H, N of Ia–j and
IIa–j are in good agreement with the calculated.
EXPERIMENTAL
IR spectra were recorded using KBr pellets on an Alpha Centauri FTIR
spectrophotometer and 1H NMR spectra on a FT-80A instrument using (CD3)2SO

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21
as solvent and Me4Si as internal standard. Elemental analyses were performed on
a Carlo-Erba 1106 Elemental Analysis instrument. Melting points were observed
in an open capillary tube and uncorrected. 4-tolyloxyacetyl chloride (22) and ary-
loxyacetic acid hydrazides (23) were prepared according to literature procedures.
Ammonium thiocyanate, glacial acetic acid, and PEG-400 were commercially
available and used as received.
General Procedure for Preparation of Ia–j
A suspension of 4-tolyloxyacetyl chloride (0.28 g, 1.5 mmol), ammonium
thiocyanate (0.20 g, 2.6 mmol) and PEG-400 (0.02 g, 0.05 mmol) in 40 mL of
methylene chloride was stirred for 1 h at room temperature, then aryloxyacetic acid
hydrazide (1.45 mmol) was added. The mixture was stirred for another 0.5 h, and a
precipitate was formed. The resulting mixture was filtered and washed with water
to remove inorganic salts. The residue was recrystallized from DMF-EtOH-H2O
to yield I as crystals. The physical and spectral results are shown below.
1-phenyloxyacetyl-4-(4-tolyloxyacetyl)-thiosemicarbazide (Ia)
White solid. Yield: 85%. m.p.: 154◦–155◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.81 (1H, s, NH), 10.03 (1H, s, NH), 9.41 (1H, s, NH), 6.70–7.44 (9H, m, ArH),
4.69 (4H, s, CH2), 2.33 (3H, s, CH3). IR (KBr, γ cm−1): 3387, 3270 (N-H), 1713
==
==
(C O), 1189 (C S). MS: m/z, 373. Anal. calcd. for C18H19N3O4S: C, 57.89; H,
5.13; N, 11.25. Found: C, 58.01; H, 5.04; N, 11.12.
1-(2-tolyloxyacetyl)-4-(4-tolyloxyacetyl)-thiosemicarbazide (Ib)
White solid. Yield: 93%. m.p.: 189◦–190◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.78 (1H, s, NH), 10.09 (1H, s, NH), 9.43 (1H, s, NH), 6.76–7.19 (8H, m, ArH),
4.66 (4H, s, CH2), 2.30 (6H, s, CH3). IR (KBr, γ cm−1): 3376, 3280 (N-H), 1710
==
==
(C O), 1195 (C S). MS: m/z, 387. Anal. calcd. for C19H21N3O4S: C, 58.90; H,
5.46; N, 10.85. Found: C, 58.72; H, 5.36; N, 10.63.
1-(4-tolyloxyacetyl)-4-(4-tolyloxyacetyl)-thiosemicarbazide (Ic)
White solid. Yield: 96%. m.p.: 167◦–168◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.80 (1H, s, NH), 10.15 (1H, s, NH), 9.38 (1H, s, NH), 6.71–7.30 (8H, m, ArH),
4.62 (4H, s, CH2), 2.26 (6H, s, CH3). IR (KBr, γ , cm−1): 3390, 3287 (N-H), 1716
==
==
(C O), 1193 (C S). MS: m/z, 387. Anal. calcd. for C19H21N3O4S: C, 58.90; H,
5.46; N, 10.85. Found: C, 58.67; H, 5.30; N, 10.57.

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WANG, LI, AND DA
1-(4-methoxylphenyloxyacetyl)-4-(4-tolyloxyacetyl)-thiosemicarbazide (Id)
White solid. Yield: 88%. m.p.: 143◦–144◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.82 (1H, s, NH), 10.21 (1H, s, NH), 9.46 (1H, s, NH), 6.72–7.20 (8H, m,
ArH), 4.70 (4H, s, CH2), 3.49 (3H, s, CH3), 2.27 (3H, s, CH3). IR (KBr, γ , cm−1):
==
==
3286, 3261 (N-H), 1718 (C O), 1190 (C S). MS: m/z, 403. Anal. calcd. for
C19H21N3O5S: C, 56.56; H, 5.25; N, 10.41. Found: C, 56.84; H, 5.31; N, 10.64.
1-(4-chlorophenyloxyacetyl)-4-(4-tolyloxyacetyl)-thiosemicarbazide (Ie)
White solid. Yield: 90%. m.p.: 157◦–158◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.77 (1H, s, NH), 10.18 (1H, s, NH), 9.54 (1H, s, NH), 6.80–7.32 (8H, m, ArH),
4.71 (4H, s, CH2), 2.31 (3H, s, CH3). IR (KBr, γ , cm−1): 3381, 3276 (N-H), 1714
==
==
(C O), 1187 (C S). MS: m/z, 407. Anal. calcd. for C18H18N3O4SCl: C, 53.00;
H, 4.45; N, 10.30. Found: C, 52.79; H, 4.31; N, 10.52.
1-(1-naphthyloxyacetyl)-4-(4-tolyloxyacetyl)-thiosemicarbazide (If)
White solid. Yield: 88%. m.p.: 177◦–178◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.68 (1H, s, NH), 10.63 (1H, s, NH), 9.43 (1H, s, NH), 6.75–7.51 (11H, m,
ArH), 4.73 (4H, s, CH2), 2.36 (3H, s, CH3). IR (KBr, γ , cm−1): 3389, 3301 (N-
==
==
H), 1713 (C O), 1186 (C S). MS: m/z, 423. Anal. calcd. for C22H21N3O4S: C,
62.40; H, 5.00; N, 9.92. Found: C, 62.27; H, 4.91; N, 10.14.
1-(2-naphthyloxyacetyl)-4-(4-tolyloxyacetyl)-thiosemicarbazide (Ig)
White solid. Yield: 92%. m.p.: 160◦–161◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.70 (1H, s, NH), 10.66 (1H, s, NH), 9.40 (1H, s, NH), 6.76–7.53 (11H, m,
ArH), 4.69 (4H, s, CH2), 2.30 (3H, s, CH3). IR (KBr, γ , cm−1): 3381, 3314 (N-
==
==
H), 1714 (C O), 1190 (C S). MS: m/z, 423. Anal. calcd. for C22H21N3O4S: C,
62.40; H, 5.00; N, 9.92. Found: C, 62.59; H, 5.07; N, 9.81.
1-(2-nitrophenyloxyacetyl)-4-(4-tolyloxyacetyl)-thiosemicarbazide (Ih)
White solid. Yield: 93%. m.p.: 206◦–207◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.80 (1H, s, NH), 10.08 (1H, s, NH), 9.42 (1H, s, NH), 6.77–7.45 (8H, m, ArH),

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23
4.69 (4H, s, CH2), 2.26 (3H, s, CH3). IR (KBr, γ , cm−1): 3376, 3281 (N-H), 1708
==
==
(C O), 1186 (C S). MS: m/z, 418. Anal. calcd. for C18H18N4O6S: C, 51.67; H,
4.34; N, 13.39. Found: C, 51.84; H, 4.30; N, 13.59.
1-(3-nitrophenyloxyacetyl)-4-(4-tolyloxyacetyl)-thiosemicarbazide (Ii)
White solid. Yield: 90%. m.p.: 171◦–172◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.85 (1H, s, NH), 10.13 (1H, s, NH), 9.46 (1H, s, NH), 6.89–7.53 (8H, m, ArH),
4.73 (4H, s, CH2), 2.37 (3H, s, CH3). IR (KBr, γ , cm−1): 3384, 3286 (N-H), 1712
==
==
(C O), 1187 (C S). MS: m/z, 418. Anal. calcd. for C18H18N4O6S: C, 51.67; H,
4.34; N, 13.39. Found: C, 51.51; H, 4.20; N, 13.19.
1-(4-nitrophenyloxyacetyl)-4-(4-tolyloxyacetyl)-thiosemicarbazide (Ij)
White solid. Yield: 95%. m.p.: 184◦–185◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.77 (1H, s, NH), 10.16 (1H, s, NH), 9.60 (1H, s, NH), 6.73–7.51 (8H, m, ArH),
4.76 (4H, s, CH2), 2.38 (3H, s, CH3). IR (KBr, γ , cm−1): 3391, 3293 (N-H), 1709
==
==
(C O), 1185 (C S). MS: m/z, 418. Anal. calcd. for C18H18N4O6S: C, 51.67; H,
4.34; N, 13.39. Found: C, 51.73; H, 4.31; N, 13.42.
General Procedure for the Preparation of Compounds IIa–j
A mixture of compound I (0.5 mol) and glacial acetic acid (5 mL) was irra-
diated in a microwave oven at 375W for 5 min, and the completion of the reaction
was monitored by TLC. The excess of glacial acetic acid was removed by evapo-
ration, the residue was poured into ice (100 g), and the precipitate was collected by
filtration and washed with water (3 × 20 mL). The product was obtained as white
crystals after recrystallization from DMF-EtOH-H2O. The physical and spectral
data of compounds IIa–j are shown below.
2-(4-tolyloxyacetylamido)-5-phenyloxymethyl-1,3,4-thiadiazole (IIa)
White solid. Yield: 92%. m.p.: 173◦–174◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.87 (1H, s, NH), 7.18–8.01 (9H, m, Ar-H), 5.58 (2H, s, CH2), 4.87 (2H, s,
CH2), 2.20 (3H, s, CH3). IR (KBr, γ , cm−1): 3166 (N-H), 1707 (C O), 1591,
==
==
==
1486, 1301, 1063 (C N-N-C S). MS: m/z, 355. Anal. calcd. for C18H17N3O3S:
C, 60.83; H, 4.82; N, 11.82. Found: C, 60.98; H, 4.79; N, 11.76.

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WANG, LI, AND DA
2-(4-tolyloxyacetylamido)-5-(2-tolyloxymethyl)-1,3,4-thiadiazole (IIb)
White solid. Yield: 95%. m.p.: 182◦–183◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.92 (1H, s, NH), 6.80–8.03 (8H, m, Ar-H), 5.60 (2H, s, CH2), 4.90 (2H, s,
CH2), 2.19 (6H, s, CH3), IR (KBr, γ , cm−1): 3164 (N-H), 1708 (C O), 1510,
==
==
==
1495, 1306, 1060 (C N-N-C S). MS: m/z, 369. Anal. calcd. for C19H19N3O3S:
C, 61.77; H, 5.18; N, 11.37. Found: C, 61.56; H, 4.83; N, 11.21.
2-(4-tolyloxyacetylamido)-5-(4-tolyloxymethyl)-1,3,4-thiadiazole (IIc)
White solid. Yield: 91%. m.p.: 188◦–189◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.89 (1H, s, NH), 6.79–8.01 (8H, m, Ar-H), 5.61 (2H, s, CH2), 4.89 (2H, s,
CH2), 2.21 (6H, s, CH3). IR (KBr, γ , cm−1): 3168 (N-H), 1711 (C O), 1509,
==
==
==
1488, 1306, 1061 (C N-N-C S). MS: m/z, 369. Anal. calcd. for C19H19N3O3S:
C, 61.77; H, 5.18; N, 11.37. Found: C, 61.86; H, 5.03; N, 11.49.
2-(4-tolyloxyacetylamido)-5-(4-methoxylphenyloxymethyl)-1,3,
4-thiadiazole (IId)
White solid. Yield: 96%. m.p.: 170◦–171◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.90 (1H, s, NH), 6.71–7.86 (8H, m, Ar-H), 5.58 (2H, s, CH2), 4.70 (2H, s,
CH2), 3.86 (3H, s, CH3), 2.19 (3H, s, CH3). IR (KBr, γ , cm−1): 3178 (N-H), 1691
==
==
==
(C O), 1509, 1463, 1309, 1081 (C N-N-C S). MS: m/z, 385. Anal. calcd. for
C19H19N3O4S: C, 59.21; H, 4.97; N, 10.90. Found: C, 59.46; H, 5.09; N, 11.16.
2-(4-tolyloxyacetylamido)-5-(4-chlorophenyloxymethyl)-1,3,4-thiadiazole (IIe)
White solid. Yield: 93%. m.p.: 185◦–186◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.88 (1H, s, NH), 6.79–8.28 (8H, m, Ar-H), 5.59 (2H, s, CH2), 4.81 (2H, s,
CH2), 2.18 (3H, s, CH3). IR (KBr, γ , cm−1): 3196 (N-H), 1697 (C O), 1512, 1492,
==
==
==
1326, 1040 (C N-N-C S). MS: m/z, 389. Anal. calcd. for C18H16N3O3SCl: C,
55.45; H, 4.14; N, 10.78. Found: C, 55.61; H, 4.30; N, 10.93.
2-(4-tolyloxyacetylamido)-5-(1-naphthyloxymethyl)-1,3,4-thiadiazole (IIf)
White solid. Yield: 97%. m.p.: 190◦–191◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.92 (1H, s, NH), 6.78–7.90 (11H, m, Ar-H), 5.63 (2H, s, CH2), 4.90 (2H, s,
CH2), 2.20 (3H, s, CH3). IR (KBr, γ , cm−1): 3201 (N-H), 1711 (C O), 1510,
==
==
==
1489, 1301, 1070 (C N-N-C S). MS: m/z, 405. Anal. calcd. for C22H19N3O3S:
C, 65.17; H, 4.72; N, 10.36 Found: C, 65.22; H, 4.63; N, 10.53.

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2-(4-tolyloxyacetylamido)-5-(2-naphthyloxymethyl)-1,3,4-thiadiazole (IIg)
25
White solid. Yield: 96%. m.p.: 181◦–182◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.90 (1H, s, NH), 6.76–7.89 (11H, m, Ar-H), 5.66 (2H, s, CH2), 4.89 (2H, s,
CH2), 2.19 (3H, s, CH3). IR (KBr, γ , cm−1): 3179 (N-H), 1708 (C O), 1513,
==
==
==
1490, 1306, 1061 (C N-N-C S). MS: m/z, 405. Anal. calcd. for C22H19N3O3S:
C, 65.17; H, 4.72; N, 10.36 Found: C, 65.31; H, 4.66; N, 10.49.
2-(4-tolyloxyacetylamido)-5-(2-nitrophenyloxymethyl)-1,3,4-thiadiazole (IIh)
White solid. Yield: 94%. m.p.: 218◦–219◦C. 1H NMR (80 MHz, DMSO-d6)
δ 12.98 (1H, s, NH), 6.99–8.31 (8H, m, Ar-H), 5.69 (2H, s, CH2), 4.89 (2H, s,
CH2), 2.21 (3H, s, CH3). IR (KBr, γ , cm−1): 3188 (N-H), 1712 (C O), 1510,
==
==
==
1495, 1304, 1071 (C N-N-C S). MS: m/z, 400. Anal. calcd. for C18H16N4O5S:
C, 53.99; H, 4.03; N, 13.99. Found: C, 53.85; H, 4.10; N, 13.82.
2-(4-tolyloxyacetylamido)-5-(3-nitrophenyloxymethyl)-1,3,4-thiadiazole (IIi)
White solid. Yield: 96%. m.p.: 187◦–188◦C. 1H NMR (80 MHz, DMSO-d6)
δ 13.03 (1H, s, NH), 6.93–8.29 (8H, m, Ar-H), 5.71 (2H, s, CH2), 4.91 (2H, s,
CH2), 2.22 (3H, s, CH3). IR (KBr, γ , cm−1): 3191 (N-H), 1703 (C O), 1511,
==
==
==
1493, 1307, 1079 (C N-N-C S). MS: m/z, 400. Anal. calcd. for C18H16N4O5S:
C, 53.99; H, 4.03; N, 13.99. Found: C, 53.88; H, 4.09; N, 13.89.
2-(4-tolyloxyacetylamido)-5-(4-nitrophenyloxymethyl)-1,3,4-thiadiazole (IIj)
White solid. Yield: 95%. m.p.: 206◦–207◦C. 1H NMR (80 MHz, DMSO-d6)
δ 13.01 (1H, s, NH), 7.01–8.33 (8H, m, Ar-H), 5.68 (2H, s, CH2), 4.87 (2H, s,
CH2), 2.19 (3H, s, CH3). IR (KBr, γ , cm−1): 3186 (N-H), 1717 (C O), 1510,
==
==
==
1496, 1305, 1072 (C N-N-C S). MS: m/z, 400. Anal. calcd. for C18H16N4O5S:
C, 53.99; H, 4.03; N, 13.99. Found: C, 53.86; H, 4.08; N, 13.87.
ACKNOWLEDGMENT
The authors thank the Natural Science Foundation of Gansu Province for
the financial support of this work.

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Received in the U.K. January 17, 2000

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