A new route to 2-(5-aryl-2-furoylamido)-5-aryloxymethyl-1,3,4-thiadiazoles

Article abstract of DOI:10.1081/SCC-120003160

The 2-(5-aryl-2-furoylamido)-5-aryloxymethyl-1,3,4-thiadiazoles 4_1-18 are synthesized by the reaction of 5-aryl-2-furoic acids 1 with phenylsulfonyl chloride and 2-amino-5-aryloxymethyl-1,3,4-thiadiazoles 3 under phase transfer catalysis.

Full text of DOI:10.1081/SCC-120003160

This article was downloaded by: [Duke University Libraries]
On: 05 January 2015, At: 10:04
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House,
37-41 Mortimer Street, London W1T 3JH, UK
Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic
Chemistry
Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
A NEW ROUTE TO 2-(5-ARYL-2-FUROYLAMIDO)-5-
ARYLOXYMETHYL-1,3,4-THIADIAZOLES
Xicun Wang a , Zheng Li a & Yuxia Da a
a Department of Chemistry , Northwest Normal University , Lanzhou, Gansu, 730070, P.R.
China
Published online: 21 Aug 2006.
To cite this article: Xicun Wang , Zheng Li & Yuxia Da (2002) A NEW ROUTE TO 2-(5-ARYL-2-FUROYLAMIDO)-5-
ARYLOXYMETHYL-1,3,4-THIADIAZOLES, Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 32:7, 1105-1111, DOI: 10.1081/SCC-120003160
To link to this article: http://dx.doi.org/10.1081/SCC-120003160
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained
in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the
Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and
should be independently verified with primary sources of information. Taylor and Francis shall not be liable for
any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever
or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of
the Content.
This article may be used for research, teaching, and private study purposes. Any substantial or systematic
reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any
form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://
www.tandfonline.com/page/terms-and-conditions

SYNTHETIC COMMUNICATIONS, 32(7), 1105–1111 (2002)
A NEW ROUTE TO
2-(5-ARYL-2-FUROYLAMIDO)-5-
ARYLOXYMETHYL-1,3,4-THIADIAZOLES
*
Xicun Wang, Zheng Li, and Yuxia Da
Department of Chemistry, Northwest Normal
University, Lanzhou, Gansu, 730070, P.R. China
ABSTRACT
The 2-(5-aryl-2-furoylamido)-5-aryloxymethyl-1,3,4-thiadia-
zoles 41–18 are synthesized by the reaction of 5-aryl-2-furoic
acids 1 with phenylsulfonyl chloride and 2-amino-5-aryloxy-
methyl-1,3,4-thiadiazoles 3 under phase transfer catalysis.
5-Aryl-2-furoic acid derivatives have been used as antibacterial agent,1
local anesthesia,2 analgesic3 and plant-growth regulator.4–5 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 anticonvulsant,14 cardiotonic,15 antihypertensive,16 antiinflam-
matory17 and antiulcer18 activity. In view of the above facts, we report herein
the preparation of a new series of compounds bearing both 5-aryl-2-furoyl
and 1,3,4-thiadiazole moiety, with the objective of obtaining new biologi-
cally active compounds.
Generally, the 2-acylamido-1,3,4-thiadiazoles are synthesized via cycli-
zation of 4-acyl-thiosemicarbazides in the presence of acid.8 However, in
*Corresponding author.
1105
Copyright & 2002 by Marcel Dekker, Inc.
www.dekker.com

1106
WANG, LI, AND DA
this paper we report a new route to 2-acylamido-5-substituted-1,3,4-thiadia-
zoles 4 by the reaction of 2-amino-5-substituted-1,3,4-thiadiazoles 3 with 5-
aryl-2-furoic acid 1 in the presence of phenylsulfonyl chloride. Although the
reactivity of the amino group in 1,3,4-thiadiazoles 3 is very low because of
the steric hindrance, we are still able to synthesize the title compounds 4
successfully using phase transfer catalysis.5,19–21
Refluxing of 5-aryl-2-furoic acids 1 with phenylsulfonyl chloride and
potassium carbonate catalyzed by polyethylene glycol-400 (PEG-400) in
acetonitrile gives 5-aryl-2-furoyl phenylsulfonates 2 as intermediate, which
on treatment with 2-amino-5-aryloxymethyl-1,3,4-thiadiazoles 3 in situ
afford 2-(5-aryl-2-furoylamido)-5-aryloxymethyl-1,3,4-thiadiazoles 41–18 in
excellent yield (Scheme).
Scheme.
The characterization of compounds 41–18 is based on their IR(KBr),
1H NMRand elemental analyses. The IRspectra exhibit a characteristic
1
strong absorption at 1665–1681 cmꢀ1 for carbonyl. The H NMRspectral
data of 41–18 in d6-dimethylsulfoxide show peaks at 13.17–13.50 (NH) and
5.39–5.50 ppm (CH2). All found of C, H, N of 41–18 are in good agreement
with the calculated.
EXPERIMENTAL
IRspectra were recorded using KBr pellets on an Alpha Centauri
FTIRspectrophotometer and 1H NMRspectra on an FT-80A instrument
using (CD3)2SO as solvent and Me4Si as an internal standard. Elemental
analyses were performed on a Carlo-Erba 1106 Elemental Analysis instru-

5-ARYL-2-FUROYL AND 1,3,4-THIADIAZOLE MOIETY
1107
ment. Melting points were observed in an open capillary tube and uncor-
rected. 5-Aryl-2-furoic acids 122 and 2-amino-5-aryloxymethyl-1,3,4-thiadia-
zoles 323,24 were prepared according to literature procedures. Phenylsulfonyl
chloride and PEG-400 were commercially available and used as received.
General Procedure for Preparation of 41–18
A mixture of 5-aryl-2-furoic acid 1 (1 mmol), K2CO3 (0.55 g, 4 mmol),
phenylsulfonyl chloride (0.18 g, 1 mmol) and PEG-400 (0.01 g, 0.03 mmol)
in 15 ml of acetonitrile was refluxed for 0.5 h, then 2-amino-5-aryloxy-
methyl-1,3,4-thiadiazole 3 (1 mmol) was added. The resulting mixture was
refluxed for another 1 h. The solvent was removed under reduced pressure,
and the residue was washed with water. The resulting solid was recrystal-
lized from DMF–EtOH–H2O (5 : 4 : 1) to yield 41–18 as crystals. The physical
and spectral results of 41–18 are shown below.
2-(5-(4-Chlorophenyl)-2-furoylamido)-5-phenyloxymethyl-1,3,4-thiadia-
zole (41): White solid. Yield: 90%. m.p.: 235–236ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.17 (1H, s, NH), 7.0–8.4 (11H, m, Ar-H and Fu-H), 5.39
(2H, s, CH2). IR(KBr, n cmꢀ1): 3148 (N-H), 1669 (C¼O), 1601, 1511, 1476,
1097 (C¼N-N¼C-S). Anal. calcd for C20H14N3O3SCl: C, 58.32; H, 3.43; N,
10.20. Found: C, 58.46; H, 3.36; N, 10.37.
2-(5-(4-Chlorophenyl)-2-furoylamido)-5-(2-tolyloxymethyl)-1,3,4-thiadia-
zole (42): White solid. Yield: 93%. m.p.: 221–222ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.20 (1H, s, NH), 7.0–8.5 (10H, m, Ar-H and Fu-H),
5.41 (2H, s, CH2), 2.30 (3H, s, CH3). IR(KBr, n cmꢀ1): 3140 (N-H), 1677
(C¼O), 1601, 1526, 1477, 1092 (C¼N-N¼C-S). Anal. calcd for
C21H16N3O3SCl: C, 59.22; H, 3.79; N, 9.87. Found: C, 59.50; H, 3.96;
N, 10.02.
2-(5-(4-Chlorophenyl)-2-furoylamido)-5-(3-tolyloxymethyl)-1,3,4-thiadia-
zole (43): White solid. Yield: 96%. m.p.: 203–204ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.26 (1H, s, NH), 7.0–8.5 (10H, m, Ar-H and Fu-H), 5.42
(2H, s, CH2), 2.28 (3H, s, CH3). IR(KBr, n cmꢀ1): 3150 (N-H), 1665
(C¼O), 1608, 1513, 1475, 1096 (C¼N-N¼C-S). Anal. calcd for
C21H16N3O3SCl: C, 59.22; H, 3.79; N, 9.87. Found: C, 59.01; H, 3.82; N, 9.96.
2-(5-(4-Chlorophenyl)-2-furoylamido)-5-(4-tolyloxymethyl)-1,3,4-thiadia-
zole (44): White solid. Yield: 95%. m.p.: 201–202ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.21 (1H, s, NH), 7.0–8.4 (10H, m, Ar-H and Fu-H), 5.46
(2H, s, CH2), 2.26 (3H, s, CH3). IR(KBr, n cmꢀ1): 3151 (N-H), 1670
(C¼O), 1599, 1516, 1474, 1090 (C¼N-N¼C-S). Anal. calcd for
C21H16N3O3SCl: C, 59.22; H, 3.79; N, 9.87. Found: C, 59.49; H, 3.99; N, 9.98.

1108
WANG, LI, AND DA
2-(5-(4-Chlorophenyl)-2-furoylamido)-5-(4-methoxylphenyloxymethyl)-
1,3,4-thiadiazole (45): White solid. Yield: 92%. m.p.: 196–197ꢁC. H NMR
(80MHz, DMSO-d6) d 13.23 (1H, s, NH), 7.0–8.4 (10H, m, Ar-H and Fu-H),
5.45 (2H, s, CH2), 3.40 (3H, s, CH3). IR(KBr, n cmꢀ1): 3147 (N-H),
1668 (C¼O), 1611, 1509, 1478, 1101 (C¼N-N¼C-S). Anal. calcd for
C21H16N3O4SCl: C, 57.08; H, 3.65; N, 9.51. Found: C, 57.29; H, 3.71; N, 9.72.
2-(5-(4-Chlorophenyl)-2-furoylamido)-5-(4-chlorophenyloxymethyl)-
1
1,3,4-thiadiazole (46): White solid. Yield: 94%. m.p.: 213–214ꢁC. H NMR
1
(80 MHz, DMSO-d6) d 13.25 (1H, s, NH), 7.0–8.5 (10H, m, Ar-H and
Fu-H), 5.40 (2H, s, CH2). IR(KBr, n cmꢀ1): 3152 (N-H), 1669 (C¼O),
1607, 1510, 1473, 1105 (C¼N-N¼C-S). Anal. calcd for C20H13N3O3SCl2:
C, 53.82; H, 2.94; N, 9.41. Found: C, 54.03; H, 3.07; N, 9.60.
2-(5-(4-Chlorophenyl)-2-furoylamido)-5-(1-naphthyloxymethyl)-1,3,4-
thiadiazole (47): White solid. Yield: 96%. m.p.: 238–239ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.26 (1H, s, NH), 7.0–8.4 (13H, m, Ar-H and
Fu-H), 5.42 (2H, s, CH2). IR(KBr, n cmꢀ1): 3184 (N-H), 1669 (C¼O),
1601, 1515, 1481, 1107 (C¼N-N¼C-S). Anal. calcd. for C24H16N3O3SCl:
C, 62.40; H, 3.49; N, 9.10. Found: C, 62.29; H, 3.32; N, 8.90.
2-(5-(4-Chlorophenyl)-2-furoylamido)-5-(4-nitrophenyloxymethyl)-1,3,4-
thiadiazole (48): White solid. Yield: 91%. m.p.: 234–235ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.27 (1H, s, NH), 7.1–8.5 (10H, m, Ar-H and
Fu-H), 5.50 (2H, s, CH2). IR(KBr, n cmꢀ1): 3118 (N-H), 1678 (C¼O),
1617, 1526, 1476, 1094 (C¼N-N¼C-S). Anal. calcd for C20H13N4O5SCl:
C, 52.58; H, 2.87; N, 12.26. Found: C, 52.72; H, 2.94; N, 12.37.
2-(5-(4-Chlorophenyl)-2-furoylamido) -5-(3-nitrophenyloxymethyl)-
1,3,4-thiadiazole (49): White solid. Yield: 93%. m.p.: 240–241ꢁC. H NMR
1
(80 MHz, DMSO-d6) d 13.28 (1H, s, NH), 7.1–8.5 (10H, m, Ar-H and Fu-
H), 5.48 (2H, s, CH2). IR(KBr, n cmꢀ1): 3150 (N-H), 1677 (C¼O), 1620,
1518, 1477, 1099 (C¼N-N¼C-S). Anal. calcd for C20H13N4O5SCl: C, 52.58;
H, 2.87; N, 12.26. Found: C, 52.69; H, 2.88; N, 12.38.
2-(5-(4-Chlorophenyl)-2-furoylamido)-5-(2,4-dichlorophenyloxymethyl)-
1,3,4-thiadiazole (410): White solid. Yield: 89%. m.p.: 212–213ꢁC. H NMR
1
(80 MHz, DMSO-d6) d 13.25 (1H, s, NH), 7.0–8.5 (9H, m, Ar-H and Fu-H),
5.46 (2H, s, CH2). IR(KBr, n cmꢀ1): 3146 (N-H), 1676 (C¼O), 1613, 1514,
1470, 1101 (C¼N-N¼C-S). Anal. calcd for C20H12N3O3SCl3: C, 49.86;
H, 2.72; N, 8.72. Found: C, 50.01; H, 2.80; N, 8.90.
2-(5-(2-Nitrophenyl)-2-furoylamido)-5-phenyloxymethyl-1,3,4-thiadia-
zole (411): White solid. Yield: 93%. m.p.: 232–233ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.40 (1H, s, NH), 6.8–8.1 (11H, m, Ar-H and Fu-H), 5.40
(2H, s, CH2). IR(KBr, n cmꢀ1): 3119 (N-H), 1670 (C¼O), 1603, 1508, 1456,
1103 (C¼N-N¼C-S). Anal. calcd for C20H14N4O5S: C, 56.87; H, 3.34; N,
13.26. Found: C, 57.06; H, 3.40; N, 13.36.

5-ARYL-2-FUROYL AND 1,3,4-THIADIAZOLE MOIETY
1109
2-(5-(2-Nitrophenyl)-2-furoylamido)-5-(2-tolyloxymethyl)-1,3,4-thiadia-
zole (412): White solid. Yield: 92%. m.p.: 246–247ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.42 (1H, s, NH), 6.8–8.2 (10H, m, Ar-H and Fu-H), 5.43
(2H, s, CH2), 2.25 (3H, s, CH3). IR(KBr, n cmꢀ1): 3167 (N-H), 1681 (C¼O),
1601, 1520, 1470, 1100 (C¼N-N¼C-S). Anal. calcd for C21H16N4O5S:
C, 57.79; H, 3.70; N, 12.84. Found: C, 57.91; H, 3.77; N, 12.98.
2-(5-(2-Nitrophenyl)-2-furoylamido)-5-(3-tolyloxymethyl)-1,3,4-thiadia-
zole (413): White solid. Yield: 90%. m.p.: 236–237ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.50 (1H, s, NH), 6.8–8.3 (10H, m, Ar-H and Fu-H),
5.44 (2H, s, CH2), 2.28 (3H, s, CH3). IR(KBr, n cmꢀ1): 3170 (N-H), 1679
(C¼O), 1605, 1513, 1465, 1098 (C¼N-N¼C-S). Anal. calcd for
C21H16N4O5S: C, 57.79; H, 3.70; N, 12.84. Found: C, 57.60; H, 3.68;
N, 12.76.
2-(5-(2-Nitrophenyl)-2-furoylamido)-5-(4-tolyloxymethyl)-1,3,4-thiadia-
zole (414): White solid. Yield: 96%. m.p.: 250–251ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.46 (1H, s, NH), 6.9–8.3 (10H, m, Ar-H and Fu-H), 5.41
(2H, s, CH2), 2.26 (3H, s, CH3). IR(KBr, n cmꢀ1): 3162 (N-H), 1677 (C¼O),
1616, 1520, 1457, 1100 (C¼N-N¼C-S). Anal. calcd for C21H16N4O5S:
C, 57.79; H, 3.70; N, 12.84. Found: C, 57.96; H, 3.73; N, 12.92.
2-(5-(2-Nitrophenyl)-2-furoylamido)-5-(4-methoxylphenyloxymethyl)-
1,3,4-thiadiazole (415): White solid. Yield: 94%. m.p.: 231–232ꢁC. H NMR
1
(80 MHz, DMSO-d6) d 13.38 (1H, s, NH), 6.8–8.3 (10H, m, Ar-H and Fu-
H), 5.42 (2H, s, CH2), 3.36 (3H, s, CH3). IR(KBr, n cmꢀ1): 3171 (N-H),
1680 (C¼O), 1620, 1523, 1470, 1099 (C¼N-N¼C-S). Anal. calcd for
C21H16N4O6S: C, 55.75; H, 3.56; N, 12.38. Found: C, 55.96; H, 3.64;
N, 12.54.
2-(5-(2-Nitrophenyl)-2-furoylamido)-5-(4-chlorophenyloxymethyl)-1,3,4-
thiadiazole (416): White solid. Yield: 95%. m.p.: 228–229ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.42 (1H, s, NH), 6.8–8.2 (10H, m, Ar-H and
Fu-H), 5.44 (2H, s, CH2). IR(KBr, n cmꢀ1): 3183 (N-H), 1676 (C¼O),
1621, 1518, 1476, 1110 (C¼N-N¼C-S). Anal. calcd for C20H13N4O5SCl:
C, 52.58; H, 2.87; N, 12.26. Found: C, 52.31; H, 2.73; N, 12.08.
2-(5-(2-Nitrophenyl)-2-furoylamido)-5-(1-naphthyloxymethyl)-1,3,4-
thiadiazole (417): White solid. Yield: 90%. m.p.: 260–261ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.47 (1H, s, NH), 6.8–8.2 (13H, m, Ar-H and
Fu-H), 5.50 (2H, s, CH2). IR(KBr, n cmꢀ1): 3159 (N-H), 1680 (C¼O),
1611, 1523, 1480, 1099 (C¼N-N¼C-S). Anal. calcd for C24H16N4O5S:
C, 61.01; H, 3.41; N, 11.86. Found: C, 61.27; H, 3.50; N, 11.98.
2-(5-(2-Nitrophenyl)-2-furoylamido)-5-(4-nitrophenyloxymethyl)-1,3,4-
thiadiazole (418): White solid. Yield: 95%. m.p.: 231–232ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.41 (1H, s, NH), 6.9–8.4 (10H, m, Ar-H and
Fu-H), 5.47 (2H, s, CH2). IR(KBr, n cmꢀ1): 3169 (N-H), 1677 (C¼O),

1110
WANG, LI, AND DA
1609, 1510, 1480, 1101 (C¼N-N¼C-S). Anal. calcd for C20H13N5O7S:
C, 51.39; H, 2.80; N, 14.98. Found: C, 51.56; H, 2.76; N, 15.09.
ACKNOWLEDGMENT
The authors thank the Natural Science Foundation of Gansu Province
for the financial support of this work.
REFERENCES
1. Dai, Y.J.; Li, Y.J.; Chen, J.C. Youji Huaxue 1988, 8, 443; Chem.
Abstr. 110: 94889.
2. Koretskaya, N.I.; Trubitsksyna, T.K.; Mashkovskii, M.D.; Oleinik,
A.F. Khim, Farm. Zh. 1977, 11, 33; Chem. Abstr. 87: 39715.
3. Burch, H.A.; Write, R.E.; Wright, G.C.; Goldenberg, M.M. J. Pharm.
Sci. 1980, 69, 107.
4. Wei, T.B.; Chen, J.C.; Wang, X.C.; Yang, S.C. Chem. J. Chin. Univ.
(Chinese), 1992, 13, 1217; Chem. Abstr. 118: 191447.
5. Wang, X.C.; Chen, J.C.; Wang, X.C. Chem. J. Chin. Univ. (Chinese),
1998, 19, 1274; Chem. Abstr. 129: 275795.
6. Eweiss, N.F.; Bahajaj, A.A. J. Heterocycl. Chem. 1987, 24, 1173.
7. Shah, V.H.; Patel, H.H.; Parikh, A.R. J. Indian Chem. Soc. 1982, 59,
678.
8. Rollas, S.; Karakus, S.; Durgun, B.B.; Kiraz, M.; Erdeniz, H. Farmaco
1996, 51, 811.
9. Mamolo, M.; Vio, L.; Banfi, E. Farmaco 1996, 51, 71.
10. Desai, K.; Baxi, A.J. J. Indian Chem. Soc. 1992, 69, 212.
11. Mandour, A.H.; Fawzy, N.M.; El-Shihi, T.H.; El-Bazza, Z.E. Pak. J.
Sci. Ind. Res. 1995, 38, 402; Chem. Abstr. 127: 135773.
12. Kidwai, M.; Misra, P.; Kumar, R.; Saxena, R.K.; Gupta, R.;
Bradoo, S. Monatsh. Chem. 1998, 129, 961.
13. Mazzone, G.; Pignatello, R.; Mazzone, S.; Panico, A.; Pennisi, G.
Farmaco 1993, 48, 1207.
14. Chufan, E.E.; Pedregosa, J.C.; Badini, O.N.; Bruno-Blanch, L.
Farmaco 1999, 54, 838.
15. Nomoto, Y.; Takai, H.; Hirata, T.; Teranishi, M.; Ohno, T.; Kubo, K.
Chem. Pharm. Bull. 1991, 39, 86.
16. Vio, L.; Mamolo, M.G.; Laneve, A. Farmaco 1989, 44, 165.
17. Amir, M.; Oberoi, A.; Alam, S. Indian. J. Chem. Sect. B 1999, 38, 237.

5-ARYL-2-FUROYL AND 1,3,4-THIADIAZOLE MOIETY
1111
18. Nishino, C.; Sato, F.; Uetake, T.; Fukunish, H.; Kojima, N. US5912258,
1999; Chem. Abstr. 131: 31943.
19. Wang, X.C.; Li, Z.; Da, Y.X.; Chen, J.C.; Wei, T.B. Synthetic
Commun. 1999, 29, 4153.
20. Wang, X.C.; Wei, T.B.; Chen, J.C.; Li, J.R. Synthetic Commun.
1996, 26, 2765.
21. Zhang, Y.M.; Wei, T.B. Synthetic Commun. 1999, 29, 2943.
22. Krutosikova, A.; Kovac, J.; Sykova, V. Collection Czecholov. Chem.
Commun. 1976, 41, 2577.
23. Chaturvedi, B.; Tiwari, N.; Nizamuddin. Indian J. Chem. Sect. B 1989,
28, 358.
24. Wasfy, A.A.F.; Nassar, S.A.; Erissa, A.M.F. Indian J. Chem. Sect. B
1996, 35, 1218.
Received in the USA March 29, 2001