Synthesis of N,N-diaryl-N′,N′-1,4- phenylenedi(oxyacetyl)dithioureas and corresponding diureas

Article abstract of DOI:10.1081/SCC-120014046

N,N-Diaryl-N′,N′-1,4-phenylenedi(oxyacetyl)-dithioureas (3a-1) are synthesized under solid-liquid phase transfer catalysis. Meanwhile, the corresponding diureas of 3a-1, N,N-Diaryl-N′,N′-1,4-phenylenedi(oxyacetyl)-diureas (4a-1), are further synthesized b

Full text of DOI:10.1081/SCC-120014046

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SYNTHESIS OF N,N-DIARYL-N′,N′-1,4-
PHENYLENEDI(OXYACETYL)-DITHIOUREAS AND
CORRESPONDING DIUREAS
Xicun Wang a , Zheng Li b & Zongsheng Guo a
a College of Chemistry and Chemical Engineering , Northwest Normal University , Lanzhou,
Gansu, 730070, P.R. China
b College of Chemistry and Chemical Engineering , Northwest Normal University , Lanzhou,
Gansu, 730070, P.R. China
Published online: 16 Aug 2006.
To cite this article: Xicun Wang , Zheng Li & Zongsheng Guo (2002) SYNTHESIS OF N,N-DIARYL-N′,N′-1,4-
PHENYLENEDI(OXYACETYL)-DITHIOUREAS AND CORRESPONDING DIUREAS, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 32:21, 3373-3381, DOI: 10.1081/SCC-120014046
To link to this article: http://dx.doi.org/10.1081/SCC-120014046
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SYNTHETIC COMMUNICATIONS
Vol. 32, No. 21, pp. 3373–3381, 2002
SYNTHESIS OF N,N-DIARYL-N0,N0-1,4-
PHENYLENEDI(OXYACETYL)-
DITHIOUREAS AND CORRESPONDING
DIUREAS
*
Xicun Wang, Zheng Li, and Zongsheng Guo
College of Chemistry and Chemical Engineering,
Northwest Normal University, Lanzhou,
Gansu, 730070, P.R. China
ABSTRACT
N,N-Diaryl-N0,N0-1,4-phenylenedi(oxyacetyl)-dithioureas
(3a–l) are synthesized under solid–liquid phase transfer
catalysis. Meanwhile, the corresponding diureas of 3a–l,
N,N-Diaryl-N0,N0-1,4-phenylenedi(oxyacetyl)-diureas (4a–l),
are further synthesized by the reaction of 3a–l with potassium
iodate in high yield.
Thiourea derivatives have attracted much attention due to their
herbicidal,[1] antibacterial,[2] anti-HIV,[3] anti-inflammatory[4] and plant-
growth regulating[5] activity. Meanwhile urea derivatives are widely used as
medicines and agrochemicals because of their anticonvulsive,[6] herbicidal,[7]
antiacetylchlolinesterase,[8] antiulcer,[9] antineoplastic,[10] hypotensive,[11]
*Corresponding author.
3373
DOI: 10.1081/SCC-120014046
Copyright & 2002 by Marcel Dekker, Inc.
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3374
WANG, LI, AND GUO
and hypoglycemic[12] activity. In addition, aryloxyacetic acid derivatives have
also been used as herbicides and plant-growth regulators.[13–16] These
applications prompt us to synthesize some new series of compounds bearing
both thiourea and aryloxyacetyl moiety or both urea and aryloxyacetyl
moiety, with the objective of further investigating the property and structure–
activity relationship of these new compounds and obtaining new biologically
active compounds.
In this paper we report a simple, high-rate and high-yield method for
preparation of substituted dithioureas under solid–liquid phase transfer
catalysts. Meanwhile, an aqueous solution route from substituted dithioureas
to corresponding diureas is also introduced.
Reaction of 1,4-phenylenedi(oxyacetyl) dichloride (1) with ammonium
thiocyanate, using polyethylene glycol-400 (PEG-400) as catalyst, the 1,4-
phenylenedi(oxyacetyl) dithioisocyanate (2) is given as intermediate, which
in situ reacts with arylamines to afford N,N-diaryl-N0,N0-1,4-phenylene-
di(oxyacetyl)-dithioureas (3a–l) in excellent yield. Further, compounds
3a–l on gentle reflux with potassium iodate in aqueous solution afford
corresponding diureas,
diureas (4a–l), in high yield (Sch. 1).
N,N-diaryl-N0,N0-1,4-phenylenedi(oxyacetyl)-
Scheme 1.

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SUBSTITUTED DITHIOUREAS
3375
PEG-400 as a phase transfer catalyst is indispensable for these
reactions. It can easily react with NH4SCN to form complex [PEG-400-
NHþ4 ]SCNÀ, which makes the SCNÀ possible to readily react with 1 and
lead to the formation of intermediate 2. However, if no PEG-400 is used,
there is no intermediate 2 formed, therefore no any target compound 3a–l
are produced at all.
Although the many reagents of transformation of C¼S into C¼O are
introduced in the literatures, such as benzeneselenic anhydride,[17] soft NOþ
species,[18] cuprous chloride-sodium hydroxide,[19] clayfen[20] and trifluoro-
acetic anhydride,[21] they all give different side reactions. Capps and Dehn[24]
used the KIO3 as desulfuring reagent to transform the thioureas of the type
ArNHCSNHAr0 into corresponding ureas efficiently. We extend this
method to the preparation of diureas bearing acyl groups successfully.
We find that the KIO3 is quite efficient reagent for the conversion of C¼S
into C¼O. No any by-product is produced in these reactions. Moreover, the
color change of the solution from colorless to violet because of the release of
I2 in the reaction can readily indicate the starting of the reaction, and the
color change from violet to colorless because of the sublimation of I2 under
the mild reflux condition can readily indicate the termination of the
reaction. In addition, it is worthy to mention that KIO3 used in this
paper is an available reagent to identify the presence of C¼S group of the
organic compounds.
The characterization of compounds 3a–l and 4a–l is based on their IR
(KBr), 1H NMR and elemental analyses. The IR spectra exhibit a character-
istic strong absorption at 1151–1170 cmÀ1 attributable to the C¼S of the
dithioureas 3a–l. The carbonyl absorption is observed at 1661–1690 cmÀ1
for 3a–l and 1671–1698 cmÀ1 for 4a–l. The 1H NMR spectral data in
d6-dimethylsulfoxide show peaks at 12.08–12.38 (NH) and 11.68–11.82 ppm
(NH) for 3a–l, and 11.77–11.90 (NH) and 10.96–11.10 ppm (NH) for 4a–l.
All elemental analyses of 3a–l and 4a–l are good agreement with the structure
prepared.
EXPERIMENTAL
IR spectra were recorded using KBr pellets on an Alpha Centauri
1
FTIR spectrophotometer and H NMR spectra on a FT-80A instrument
using (CD3)2SO as solvent and Me4Si as internal standard. Elemental
analyses were performed on a Vario EI Elemental Analysis instrument.
Mass spectra were recorded on a QP-1000A GC-MS using the impact
mode (70 eV). Melting points were observed in an open capillary tube
and uncorrected. 1,4-Phenylenedi(oxyacetyl) dichloride (1) was prepared

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3376
WANG, LI, AND GUO
according to literature procedure.[23] Arylamines, ammonium thiocyanate,
potassium iodate and PEG-400 were commercially available and used as
received.
General Procedure for the Preparation of Compounds 3a–l
To a solution of 0.79 g (3.00 mmol) of 1,4-phenylenedi(oxyacetyl)
dichloride (1) in 15 mL of methylene dichloride, 0.40 g (5.25 mmol) of
ammonium thiocyanate and 0.04 g (0.10 mmol) of polyethylene glycol-400
were added. The mixture was stirred for 1 h at room temperature. Then
arylamine (2.95 mmol) was added and the reaction mixture was stirred for
another 0.5 h at room temperature. To the resulting mixture, 10 mL of water
was added so that the inorganic salts were dissolved, then the slurry was
filtered, the solid was washed with 3 ꢀ 5 mL water and recrystallized from
DMF–EtOH–H2O (6 : 3: 1), and the product was given. The physical and
spectral data of compounds 3a–l are reported below.
N,N-Diphenyl-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea (3a): White
solid. Yield: 90%. M.p.: 158–159ꢁC. H NMR (DMSO-d6) ꢀ 12.11 (s, 2H,
1
NH), 11.70 (s, 2H, NH), 7.04–8.20 (m, 14H, Ar-H), 4.70 (s, 4H, CH2). IR
(KBr, ꢁ, cmÀ1); 3203, 3143, 3061 (N-H), 1684 (C¼O), 1156 (C¼S). MS: m/z,
495 (Mþ). Anal. calcd. for C24H22N4O4S2: C, 58.28; H, 4.48; N, 11.33.
Found: C, 58.41; H, 4.32; N, 11.39.
N,N-Di(2-Methylphenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea
(3b): White solid. Yield: 87%. M.p.: 200–201ꢁC. H NMR (DMSO-d6) ꢀ
1
12.08 (s, 2H, NH), 11.68 (s, 2H, NH), 7.00–8.16 (m, 12H, Ar-H), 4.71 (s,
4H, CH2), 2.26 (s, 6H, CH3). IR (KBr, ꢁ, cmÀ1): 3397 (N-H), 1690 (C¼O),
1151 (C¼S). MS: m/z, 523 (Mþ). Anal. calcd. for C26H26N4O4S2: C, 59.75;
H, 5.01; N, 10.72. Found: C, 59.58; H, 4.94; N, 10.81.
N,N-Di(4-Methylphenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea
(3c): White solid. Yield: 95%. M.p.: 167–168ꢁC. H NMR (DNSO-d6) ꢀ
1
12.18 (s, 2H, NH), 11.70 (s, 2H, NH) 7.10–8.03 (m, 12H, Ar-H), 4.68
(s, 4H, CH2), 2.24 (s, 6H, CH3). IR (KBr, ꢁ, cmÀ1): 3305 (N-H), 1674
(C¼O), 1160 (C¼S). MS: m/z, 523 (Mþ). Anal. calcd. for C26H26N4O4S2:
C, 59.75; H, 5.01; N, 10.72. Found: C, 59.66; H, 5.11; N, 10.79.
N,N-Di(2-Methoxylphenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea
(3d): White solid. Yield: 94%. M.p.: 159–160ꢁC. H NMR (DMSO-d6) ꢀ
1
12.09 (s, 2H, NH), 11.69 (s, 2H, NH), 6.99–8.21 (m, 12H, Ar-H), 4.71 (s,
4H, CH2), 3.40 (s, 6H, CH3). IR (KBr, ꢁ, cmÀ1): 3267, 3204 (N-H), 1661
(C¼O), 1168 (C¼S). MS: m/z, 555 (Mþ). Anal. calcd. for C26H26N4O6S2: C,
56.30; H, 4.72; N, 10.10. Found: C, 56.54; H, 4.52; N, 10.22.

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SUBSTITUTED DITHIOUREAS
3377
N,N-Di(2-Chlorophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea
(3e): White solid. Yield: 89%. M.p.: 156–157ꢁC. H NMR (DMSO-d6) ꢀ
1
12.12 (s, 2H, NH), 11.80 (s, 2H, NH), 7.29–8.16 (m, 12H, Ar-H), 4.73
(s, 4H, CH2). IR (KBr, ꢁ, cmÀ1): 3367 (N-H), 1684 (C¼O), 1157 (C¼S).
MS: m/z, 563 (Mþ). Anal. calcd. for C24H20N4O4S2Cl2: C, 51.16; H, 3.58;
N, 9.94. Found: C, 51.26; H, 3.70; N, 9.87.
N,N-Di(4-Chlorophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea
(3f): White solid. Yield: 91%. M.p. 179–180ꢁC. H NMR (DMSO-d6) ꢀ
1
12.20 (s, 2H, NH), 11.82 (s, 2H, NH), 7.20–8.18 (m, 12H, Ar-H), 4.72 (s,
4H, CH2). IR (KBr, ꢁ, cmÀ1): 3370 (N-H), 1681 (C¼O), 1156 (C¼S). MS:
m/z, 563 (Mþ). Anal. calcd. for C24H20N4O4S2Cl2: C, 51.16; H, 3.58; N,
9.94. Found: C, 51.35; H, 3.42; N, 9.80.
N,N-Di(4-Bromophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea
(3g): White solid. Yield: 92%. M.p.: 224–225ꢁC. 1H NMR (DMSO-d6)
ꢀ 12.30 (s, 2H, NH), 11.70 (s, 2H, NH), 7.10–8.20 (m, 12H, Ar-H), 4.68
(s, 4H, CH2). IR (KBr, ꢁ, cmÀ1): 3271 (N-H), 1684 (C¼O), 1160 (C¼S). MS:
m/z, 654 (Mþ þ 2). Anal. calcd. for C24H20N4O4S2Br2: C, 44.19; H, 3.09; N,
8.59. Found: C, 44.28; H, 3.43; N, 8.25.
N,N-Di(1-Naphthyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea (3h):
White solid. Yield: 88%. M.p.: 163–164ꢁC.1H NMR (DMSO-d6) ꢀ 12.12
(s, 2H, NH), 11.68 (s, 2H, NH), 7.30–8.20 (m, 18H, Ar-H), 4.70 (s, 4H,
CH2). IR (KBr, ꢁ, cmÀ1): 3269, 3157 (N-H), 1688 (C¼O), 1164 (C¼S). MS:
m/z, 595 (Mþ). Anal. calcd. for C32H26N4O4S2: C, 64.63; H, 4.41; N, 9.42.
Found: C, 64.71; H, 4.39; N, 9.34.
N,N-Di(2-Naphthyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea (3i):
White solid. Yield: 91%. M.p.: 263–264ꢁC. H NMR (DMSO-d6) ꢀ 12.13
1
(s, 2H, NH), 11.70 (s, 2H, NH), 7.36–8.19 (m, 18H, Ar-H), 4.71 (s, 4H,
CH2). IR (KBr, ꢁ, cmÀ1): 3301, 3175 (N-H), 1690 (C¼O), 1170 (C¼S). MS:
m/z, 595 (Mþ). Anal. calcd. for C32H26N4O4S2: C, 64.63; H, 4.41; N, 9.42.
Found: C, 64.58; H, 4.29; N, 9.57.
N,N-Di(4-Nitrophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithiourea
(3j): White solid. Yield: 91%. M.p.: 194–195ꢁC. H NMR (DMSO-d6) ꢀ
1
12.38 (s, 2H, NH), 11.80 (s, 2H, NH), 7.36–8.20 (m, 12H, Ar-H), 4.76 (s,
4H, CH2). IR(KBr, ꢁ, cmÀ1): 3369 (N-H), 1701 (C¼O), 1170 (C¼S). MS:
m/z, 585 (Mþ). Anal. calcd. for C24H20N6O8S2: C, 49.31; H, 3.45; N, 14.38.
Found: C, 49.53; H, 3.43; N, 14.46.
N,N-Di(4-Acetylamidophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-dithio-
urea (3k): White solid. Yield: 86%. M.p.: 294–295ꢁC. 1H NMR (DMSO-d6) ꢀ
12.30 (s, 2H, NH), 11.78 (s, 2H, NH), 9.31 (s, 2H, NH) 7.11–8.23 (m, 12H, Ar-
H), 4.69 (s, 4H, CH2), 2.57 (s, 6H, CH3). IR (KBr, ꢁ, cmÀ1): 3294, 3056 (N-H),
1670 (C¼O), 1158 (C¼S). MS: m/z, 609 (Mþ). Anal. calcd. for C28H29N6O6S2:
C, 55.25; H, 4.64; N, 13.81. Found: C, 55.12; H, 4.78; N, 13.89.

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3378
WANG, LI, AND GUO
N,N-Di(2-Thiazolyl)-N0,N0-1,4 phenylenedi(oxyacetyl)-dithiourea (3l):
White solid. Yield: 86%. M.p.: 233–234ꢁC. H NMR (DMSO-d6) ꢀ 12.20
(s, 2H, NH), 11.68 (s, 2H, NH), 7.01–8.11 (m, 8H, Ar-H& Th-H), 4.71 (s,
4H, CH2). IR (KBr, ꢁ, cmÀ1): 3151 (N-H), 1677 (C¼O), 1168 (C¼S). MS:
m/z, 509 (Mþ). Anal. calcd. for C18H16N4O4S4: C, 42.51; H, 3.17; N, 16.52.
Found: C, 42.64; H, 3.33; N, 16.49.
1
General Procedure for the Preparation of Compounds 4a–l
A suspension of 0.50 mmol of compound 3 and 0.75 mmol (0.16 g) of
potassium iodate in 30 mL of water was refluxed for 1 h. The resulting
mixture was filtered, the solid was washed with 3 ꢀ 5 mL water and recrys-
tallized from DMF–EtOH–H2O (6 : 3 : 1), then the product was given.
The physical and spectral data of compounds 4a–l are reported below.
N,N-Diphenyl-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4a): White
solid. Yield: 97%. M.p.: 200–201ꢁC. H NMR (DMSO-d6) ꢀ 11.82 (s, 2H,
1
NH), 11.03 (s, 2H, NH), 7.02–8.18 (m, 14H, Ar-H), 4.71 (s, 4H, CH2). IR
(KBr, ꢁ, cmÀ1): 3164 (N-H), 1682 (C¼O). MS: m/z, 462 (Mþ). Anal. Calcd. for
C24H22N4O6: C, 62.33; H, 4.79; N, 12.12. Found: C, 62.11; H, 4.58; N, 12.36.
N,N-Di(2-Methylphenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4b):
White solid. Yield: 93%. M.p.: 131–132ꢁC. 1H NMR (DMSO-d6) ꢀ 11.80 (s,
2H, NH), 11.06 (s, 2H, NH), 6.96–8.10 (m, 12H, Ar-H), 4.72 (s, 4H, CH2),
2.23 (s, 6H, CH3). IR (KBr, ꢁ, cmÀ1): 3317 (N-H), 1688 (C¼O). MS: m/z,
491 (Mþ). Anal. calcd. for C26H26N4O6: C, 63.66; H, 5.34; N, 11.42. Found:
C, 63.75; H, 5.43; N, 11.68.
N,N-Di(4-Methylphenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4c):
White solid. Yield: 94%. M.p.: 203–204ꢁC. H NMR (DMSO-d6) ꢀ 11.81
1
(s, 2H, NH), 11.07 (s, 2H, NH), 7.08–8.09 (m, 12H, Ar-H), 4.69 (s, 4H,
CH2), 2.25 (s, 6H, CH3). IR (KBr, ꢁ, cmÀ1): 3305 (N-H), 1673 (C¼O). MS:
m/z, 491 (Mþ). Anal. calcd. for C26H26N4O6: C, 63.66; H, 5.34; N, 11.42.
Found: C, 63.55; H, 5.21; N, 11.62.
N,N-Di(2-Methoxylphenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea
(4d): White solid. Yield: 98%. M.p.: 165–166ꢁC. 1H NMR (DMSO-d6)
ꢀ 11.79 (s, 2H, NH), 11.06 (s, 2H, NH), 7.03–8.16 (m, 12H, Ar-H), 4.73
(s, 4H, CH2), 3.41 (s, 6H, CH3). IR (KBr, ꢁ, cmÀ1): 3302 (N-H), 1686
(C¼O). MS: m/z, 523 (Mþ). Anal. calcd. for C26H26N4O8: C, 59.77; H,
5.02; N, 10.72. Found: C, 59.61; H, 5.13; N, 10.86.
N,N-Di(2-Chlorophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4e):
White solid. Yield: 90%. M.p.: 161–162ꢁC. H NMR (DMSO-d6) ꢀ 11.81
1
(s, 2H, NH), 11.06 (s, 2H, NH), 7.10–8.06 (m, 12H, Ar-H), 4.74 (s, 4H,
CH2). IR (KBr, ꢁ, cmÀ1): 3371, 3064 (N-H), 1690 (C¼O). MS: m/z, 531

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SUBSTITUTED DITHIOUREAS
3379
(Mþ). Anal. calcd. for C24H20N4O6Cl2: C. 54.25; H, 3.79; N, 10.54. Found:
C, 54.37; H, 3.70; N, 10.69.
N,N-Di(4-Chlorophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4f):
White solid. Yield: 91%. M.p.: 196–197ꢁC. H NMR (DMSO-d6) ꢀ 11.79
1
(s, 2H, NH), 10.99 (s, 2H, NH), 7.26–8.23 (m, 12H, Ar-H), 4.73 (s, 4H,
CH2). IR (KBr, ꢁ, cmÀ1): 3300 (N-H), 1681 (C¼O). MS: m/z, 531 (Mþ).
Anal. calcd. for C24H20N4O6Cl2: C, 54.25; H, 3.79; N, 10.54. Found: C,
54.20; H, 3.62; N, 10.74.
N,N-Di(2-Bromophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4g):
White solid. Yield: 95%. M.p.: 191–192ꢁC. H NMR (DMSO-d6) ꢀ 11.83
1
(s, 2H, NH), 11.07 (s, 2H, NH), 7.19–8.18 (m, 12H, Ar-H), 4.69 (s, 4H,
CH2). IR (KBr, ꢁ, cmÀ1): 3317 (N-H), 1671 (C¼O), 1160 (C¼S). MS: m/z,
622 (Mþ þ 2). Anal. calcd. for C24H20N4O6Br2: C, 46.47; H, 3.25; N, 9.03.
Found: C, 46.61; H, 3.40; N, 9.23.
N,N-Di(1-Naphthyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4h):
White solid. Yield: 90%. M.p.: 113–114ꢁC. H NMR (DMSO-d6) ꢀ 11.77
1
(s, 2H, NH), 10.96 (s, 2H, NH), 7.26–8.09 (m, 18H, Ar-H), 4.74 (s, 4H,
CH2). IR (KBr, ꢁ, cmÀ1): 3320 (N-H), 1683 (C¼O). MS: m/z, 563 (Mþ).
Anal. calcd. for C32H26N4O6: C, 68.32; H, 4.66; N, 9.96. Found: C, 68.45;
H, 4.40; N, 9.99.
N,N-Di(2-Naphthyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4i):
White solid. Yield: 94%. M.p.: 257–258ꢁC. H NMR (DMSO-d6) ꢀ 11.80
1
(s, 2H, NH), 11.01 (s, 2H, NH), 7.30–8.13 (m, 18H, Ar-H), 4.74 (s, 4H,
CH2). IR (KBr, ꢁ, cmÀ1): 3327 (N-H), 1685 (C¼O). MS: m/z, 563 (Mþ).
Anal. calcd. for C32H26N4O6: C, 68.32; H, 4.66; N, 9.96. Found: C, 68.21;
H, 4.72; N, 9.88.
N,N-Di(4-Nitrophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4j):
White solid. Yield: 92%. M.p.: 187–188ꢁC. H NMR (DMSO-d6) ꢀ 11.90
1
(s, 2H, NH), 11.10 (s, 2H, NH), 7.23–8.21 (m, 12H, Ar-H), 4.79 (s, 4H,
CH2). IR (KBr, ꢁ, cmÀ1): 3370, 3080 (N-H), 1698 (C¼O). MS: m/z, 552
(Mþ). Anal. calcd. for C24H20N6O10: C, 52.18; H, 3.65; N, 15.21. Found: C,
52.04; H, 3.48; N, 15.36.
N,N-Di(4-Acetylamidophenyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea
(4k): White solid. Yield: 95%. M.p.: 298–299ꢁC. H NMR (DMSO-d6) ꢀ
1
11.86 (s, 2H, NH), 10.99 (s, 2H, NH), 9.31 (s, 2H, NH), 7.19–8.16 (m, 12H,
Ar-H), 4.73 (s, 4H, CH2), 2.60 (s, 6H, CH3). IR (KBr, ꢁ, cmÀ1): 3317 (N-H),
1671 (C¼O). MS: m/z, 577 (Mþ). Anal. calcd. for C28H28N6O8: C, 58.33; H,
4.89; N, 14.58. Found: C, 58.45; H, 4.79; N, 14.62.
N,N-Di(2-Thiazolyl)-N0,N0-1,4-phenylenedi(oxyacetyl)-diurea (4l): White
solid. Yield: 91%. M.p.: 251–252ꢁC. H NMR (DMSO-d6) ꢀ 11.80 (s, 2H,
1
NH), 10.98 (s, 2H, NH), 6.89–8.20 (m, 8H, Ar-H and Th-H), 4.70 (s, 4H,
CH2). IR (KBr, ꢁ, cmÀ1): 3148 (N-H), 1677 (C¼O). MS: m/z, 476 (Mþ).

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3380
WANG, LI, AND GUO
Anal. calcd. for C18H16N6O6S2: C, 45.37; H, 3.38; N, 17.64. Found: C,
45.28; H, 3.43; N, 17.79.
ACKNOWLEDGMENT
The authors thank the Scientific and Technological Innovation
Engineering of Northwest Normal University, Natural Science Foundation
of Gansu Province for the financial support of this work.
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Received in Japan July 10, 2001

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