Journal of the Iranian Chemical Society
as white solid with m.p.=179–186 °C after recrystallization
process. 1H-NMR (CDCl3, 500 MHz,): δ 1.48 (s, 9H), 2.34
(s, 3H), 4.77 (s, 1H), 4.97 (s, 2H), 10.71 (s, 1H); 13C-NMR
(CDCl3, 125 MHz): δ 21.5, 28.3, 79.9, 95.5, 154.4, 155.7,
169.6; Anal. Calcd for C9H16N2O3 (200.24): C, 53.99; H,
8.05; N, 13.99. Found: C, 53.78; H, 8.09; N, 13.73.
CDCl3): δ 3.89 (s, 3H), 5.39 (s, 2H), 6.96 (d, J= 9.0 Hz,
2H), 7.38-7.51 (m, 5H), 8.08 (d, J=9.0 Hz, 2H); 13C-NMR
(CDCl3, 75 MHz): δ 55.4, 66.4, 113.6, 122.6, 128.1, 128.2,
128.6, 131.8, 136.3, 163.4, 166.2.
Benzyl-2-bromobenzoate (5f). Following the general pro-
cedure, the product 5f was obtained in 78% yield as a yel-
low oil after column chromatography. 1H-NMR (300 MHz,
CDCl3): δ 5.43 (s, 2H), 7.35-7.54 (m, 7H), 7.68-7.71 (m,
1H), 7.85-7.88(m, 1H); 13C-NMR (CDCl3, 75 MHz): δ
67.4, 121.8, 127.2, 128.4, 128.5, 128.6, 131.5, 132.0, 132.7,
134.4, 135.5, 165.9.
Allyl(Z)-3-ureidobut-2-enoate (2f). Following the general
procedure, the product 2f was obtained in 88% yield as white
solid with m.p.=140–142 °C after recrystallization process.
1H-NMR (DMSO, 300 MHz): δ 2.28 (d, J= 0.5 Hz, 3H),
4.57 (dt, J1 =5.4 Hz, J2 =1.4 Hz, 2H), 4.83 (d, J=0.7 Hz,
1H), 5.22 (dq, J1 = 10.4 Hz, J2 = 1.3 Hz, 1H), 5.29 (dq,
J1 =17.2 Hz, J2 =1.6 Hz, 1H), 5.88-6.01 (m, 1H), 6.83 (brs,
2H), 10.13 (s, 1H); 13C-NMR (DMSO, 75 MHz): δ 22.1,
63.8, 91.8, 117.9, 133.6, 154.6, 157.8, 168.3; Anal. Calcd
for C8H12N2O3 (184.20): C, 52.17; H, 6.57; N, 15.21. Found:
C, 52.07; H, 6.46; N, 15.17.
Benzyl-2-naphthoate (5j). Following the general proce-
dure, the product 5j was obtained in 77% yield as a yellow oil
after column chromatography. 1H-NMR (300 MHz, CDCl3):
δ 5.49 (s, 2H), 7.41-7.66 (m, 7H), 7.92 (d, J=8.6 Hz, 2H),
7.99 (d, J=7.9 Hz, 1H), 8.16 (dd, J1 =8.6 Hz, J2 =1.6 Hz
1H), 8.70 (s, 1H); 13C-NMR (CDCl3, 75 MHz): δ 66.9,
125.3, 126.7, 127.4, 127.8, 128.2, 128.30, 128.4, 128.6,
129.4, 131.2, 132.5, 135.6, 136.1, 166.6.
Benzyl(Z)-3-ureidobut-2-enoate (2g). Following the gen-
eral procedure, the product 2g was obtained in 88% yield
as white solid with m.p. = 170–172 °C after recrystalliza-
tion process. 1H-NMR (DMSO, 500 MHz): δ 2.27 (s, 3H),
4.85 (s, 1H), 5.12 (s, 2H), 6.84 (brs, 2H), 7.32-7.39 (m,
5H), 10.13 (s, 1H); 13C-NMR (DMSO, 125 MHz): δ 22.1,
64.8, 91.8, 128.2, 128.9, 137.1, 154.5, 157.9, 168.4; Anal.
Calcd for C12H14N2O3 (234.26): C, 61.53; H, 6.02; N, 11.96.
Found: C, 61.48; H, 6.09; N, 11.83.
Naphthalen-1-ylmethyl benzoate (5s). Following the gen-
eral procedure, the product 5s was obtained in 90% yield
1
as a yellow oil after column chromatography. H NMR
(300 MHz, CDCl3): δ 5.88 (s, 2H), 7.43-7.76 (m, 7H), 7.91-
8.32 (m, 5H); 13C-NMR (CDCl3, 75 MHz): δ 65.1, 123.6,
125.3, 126.0, 126.6, 127.5, 128.4, 128.7, 129.3, 129.7,
130.1, 131.5, 131.8, 133.0, 133.8, 166.5.
(Z)-1-(4-oxopent-2-en-2-yl)urea (2h). Following the gen-
eral procedure, the product 2h was obtained in 95% yield
as white solid with m.p. = 186–191 °C after recrystalliza-
tion process. 1H-NMR (DMSO, 500 MHz): δ 2.02 (s, 3H),
2.26 (s, 3H), 5.28 (s, 1H), 6.88 (brs, 2H), 11.51 (s, 1H);
13C-NMR (DMSO, 125 MHz): δ 21.8, 30.27, 102.6, 154.7,
157.1, 197.9; Anal. Calcd for C6H10N2O2 (142.16): C, 50.69;
H, 7.09; N, 19.71. Found: C, 50.63; H, 7.15; N, 19.66.
(Z)-N,N-diethyl-3-ureidobut-2-enamide (2i). Follow-
ing the general procedure, the product 2i was obtained
in 80% yield as white solid with m.p. = 178–182 °C after
recrystallization process. 1H-NMR (DMSO, 300 MHz,): δ
1.05-1.11 (m, 6H), 2.26 (s, 3H), 3.31-3.33 (m, 4H), 5.03
(d, J=0.8 Hz, 1H), 6.53 (s, 2H), 11.53 (s, 1H); 13C-NMR
(DMSO, 75 MHz): δ 13.8, 15.0, 22.4, 42.0, 92.0, 153.4,
155.2, 168.0; Anal. Calcd for C9H17N3O2 (199.25): C, 54.25;
H, 8.60; N, 21.09. Found: C, 54.18; H, 8.68; N, 21.17.
Benzyl benzoate (5a). Following the general procedure,
the product 5a was obtained in 80% yield as a yellow oil after
Acknowledgements We are thankful to Persian Gulf University
Research Council for partial support of this work.
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5.43 (s, 2H), 7.40–7.53 (m, 7H), 7.61 (tt, J1 =7.3 Hz, J2 =1.
3 Hz, 1H), 8.13 (d, J=1.4 Hz, 1H), 8.16 (d, J=1.3 Hz, 1H);
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Benzyl-4-methoxybenzoate (5c). Following the general
procedure, the product 5c was obtained in 85% yield as a yel-
low oil after column chromatography. 1H-NMR (300 MHz,
1 3