J IRAN CHEM SOC
progress of reaction was monitored by TLC; n-hexane/
ethyl acetate: 9/1). After completion of the reaction, etha-
nol (8 mL) was added to the reaction mixture and heated at
2,211, 1,500, 1,461, 1,385, 1,205, 1,174, 1,085, 1,040, 995,
822.
7
0 °C for 5 min. The reaction mixture was filtered off and
was washed with hot ethanol. Then, the solution was
1-(4-Methylphenyl)-1H-1,2,3,4-tetrazole
-
1
1
cooled to room temperature and 4 mL of 4 mol L
White solid; mp: 93–94 °C; H NMR (500 MHz, CDCl ,
3
aqueous solution of HCl was added. The precipitated
product was filtered, washed with water, and dried to
obtain the pure product.
298 K): d (ppm) = 3.02 (s, 3H), 7.40 (d, J = 8.4 Hz, 2H),
7.62 (d, J = 8.4 Hz, 2H), 9.02 (s, 1H); FT-IR: m
(cm ) = 3,105, 2,211, 1,500, 1,461, 1,385, 1,205, 1,174,
max
-
1
1
Yield: 178 mg (98 %), white solid; mp: 160–162 °C; H
1,085, 1,040, 995, 822.
NMR (500 MHz, CDCl , 298 K): d (ppm) = 7.62 (2H, d,
3
J = 8.7 Hz), 7.73 (d, J = 8.7 Hz, 2H), 9.2 (s, 1H); FT-IR:
-
1-(4-Methoxyphenyl)-1H-1,2,3,4-tetrazole
1
mmax (cm ) = 3,105, 2,211, 1,500, 1,461, 1,385, 1,205,
1
1
,174, 1,085, 1,040, 995, 822.
White solid; mp: 117–118 °C; H NMR (500 MHz, CDCl ,
3
298 K): d (ppm) = 3.82 (s, 3H), 7.00 (d, J = 8.9 Hz, 2H), 7.58
-1
1
-Phenyl-1H-1,2,3,4-tetrazole
(d, J = 8.9 Hz, 2H), 9.04 (s, 1H); FT-IR: mmax (cm ) = 3,105,
,211, 1,500, 1,461, 1,385, 1,205, 1,174, 1,085, 1,040, 995, 822.
2
1
Yield: 131 mg (98 %), white solid; mp: 63–65 °C;
H
NMR (500 MHz, CDCl , 298 K): d (ppm) = 7.32 (t,
1-(4-Acetylphenyl)-1H-1,2,3,4-tetrazole
3
J = 7.4 Hz, 1H), 7.63 (t, J = 7.6 Hz, 2H), 7.76 (d,
-
1
1
J = 7.8, 2H), 9.07 (s, 1H); FT-IR: mmax (cm ) = 3,105,
White solid; mp: 174–175 °C; H NMR (500 MHz, CDCl ,
3
2
,211, 1,500, 1,461, 1,385, 1,205, 1,174, 1,085, 1,040, 995,
298 K): d (ppm) = 2.61 (s, 3H), 7.89 (d, J = 8.9 Hz, 2H),
8
22.
8.12 (d, J = 8.9 Hz, 2H), 9.37 (s, 1H); FT-IR: m
(
max
-
cm ) = 3,105, 2,211, 1,500, 1,461, 1,385, 1,205, 1,174,
1
1
-(4-Bromophenyl)-1H-1,2,3,4-tetrazole
1,085, 1,040, 995, 822.
1
Yield: 143 mg (98 %) white solid; mp: 180–181 °C; H
1-(4-Nitrophenyl)-1H-1,2,3,4-tetrazole
NMR (500 MHz, CDCl , 298 K): d (ppm) = 7.64 (d,
3
1
J = 8.1 Hz, 2H), 7.68 (d, J = 8.1 Hz, 2H), 9.23 (s, 1H);
1
Yellow solid; mp: 191–193 °C; H NMR (500 MHz, CDCl ,
3
-
FT-IR: mmax (cm ) = 3,125, 1,493, 1,383, 1,270, 1,210,
298 K): d (ppm) = 8.06 (d, J = 8.9 Hz, 2H), 8.38 (d,
J = 8.9 Hz, 2H), 9.64 (s, 1H); FT-IR: mmax (cm ) = 3,105,
,211, 1,500, 1,461, 1,385, 1,205, 1,174, 1,085, 1,040, 995, 822.
-1
1
,194, 1,178, 992, 815.
2
1
-(4-Iodophenyl)-1H-1,2,3,4-tetrazole
1
-(3-Nitrophenyl)-1H-1,2,3,4-tetrazole
1
White solid; mp: 196–197 °C; H NMR (500 MHz, CDCl ,
3
1
2
98 K): d (ppm) = 7.52 (d, J = 6.9 Hz, 2H), 7.98 (d,
J = 6.9 Hz, 2H), 9.03 (s, 1H); FT-IR: mmax (cm ) = 3,105,
,211, 1,500, 1,461, 1,385, 1,205, 1,174, 1,085, 1,040, 995, 822.
White solid; mp: 108–110 °C; H NMR (500 MHz, CDCl ,
298 K): d (ppm) = 7.78 (t, J = 8.2 Hz, 1H), 8.21 (d,
3
-1
2
Table 1 Optimization of the reaction conditions for synthesis of
1-(4-chlorophenyl)-1H-1,2,3,4-tetrazole (1 mmol) using [P -VP]N /
1
-(4-Hydroxy phenyl)-1H-1,2,3,4-tetrazole
4
3
3
CH(OEt) /AcOH
1
White solid; mp: 210–211 °C; H NMR (500 MHz,
Entry [P
VP]N
mmol)
4
-
CH(OEt)
(mmol)
3
Reaction
Reaction
Isolated
DMSO-d , 298 K): d (ppm) = 6.98 (d, J = 8.9 Hz, 2H),
3
time (min) temp. (°C) yield (%)
6
(
7
.68 (d, J = 8.9 Hz, 2H), 9.91 (s, 1H), 10.11 (s, 1H); FT-
1
-
IR: mmax (cm ) = 3,105, 2,211, 1,500, 1,461, 1,385,
1
2
3
4
5
6
7
8
3.4
2.5
2
3
10
10
30
60
10
60
60
60
100
100
100
100
100
r.t
98
98
98
51
98
0
1
,205, 1,174, 1,085, 1,040, 995, 822.
3
3
1
-(4-Ethylphenyl)-1H-1,2,3,4-tetrazole
2.5
2.5
2.5
2.5
2.5
2
2.5
2.5
2.5
2.5
1
White solid; mp: 77–78 °C; H NMR (500 MHz, CDCl ,
3
2
98 K): d (ppm) = 1.33 (t, J = 7.6 Hz, 3H), 2.79 (q,
J = 7.6 Hz, 2H), 7.44 (d, J = 8.2 Hz, 2H), 7.65 (d,
65
50
78
75
-1
J = 8.2 Hz, 2H), 9.00 (s, 1H); FT-IR: mmax (cm ) = 3,105,
123