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1 mL), acetonitrile (2 mL), and sulfamic acid (10
mol%) in a 10-mL round bottom flask equipped with
a magnetic stirrer were stirred at room temperature
for 6 h. After completion of the reaction, as indicated
by TLC, the reaction mixture was extracted with
diethyl ether (5 × 10 mL). The combined organic
layers were dried, and then concentrated in vacuum.
The products were analyzed through GC/MS.
ANALYTICAL DATA FOR SELECTED
COMPOUNDS
1
1-Butyl-2,5-dimethyl-1H-pyrrole: Pale yellow oil; H
NMR (300 MHz, CDCl3) δH (ppm): 0.95 (t, J = 7 Hz,
CH3, 3H), 1.36 (m, CH2, 2H), 1.58 (m, CH2, 2H), 2.19
(s, CH3, 6H), 3.69 (t, J = 8.3 Hz, CH2, 2H), 5.78 (s,
pyrrolics, 2H); GC/MS (m/z): M+ 151, 136, 122, 108,
94; Anal. Calcd for C10H17N: C, 79.41; H, 11.33; N,
9.26. Found: C, 79.38; H, 11.37; N, 9.25.
1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole:
Yellow solid, mp 57–59◦C; 1H NMR (300 MHz,
CDCl3) δH (ppm): 2.04 (CH3, s, 6H), 3.88 (OCH3,
s, 3H), 5.90 (pyrrolics, s, 2H), 6.94 (PhH, d, 2H,
J = 8.89 Hz), 7.15 (d, PhH, 2H, J = 8.90 Hz); GC/MS
(m/z): M+ 201, 186, 171, 159, 145, 129. Anal. Calcd
for C13H15NO: C, 77.58; H, 7.51; N, 6.96. Found: C,
77.56; H, 7.55; N, 6.94.
1-Phenyl-2,5-dimethyl-1H-pyrrole: White solid,
1
mp 50–51◦C; H NMR (300 MHz, CDCl3) δH (ppm):
2.05 (CH3, s, 6H), 5.93 (pyrrolics, s, 2H), 7.22–7.25
(PhH, m, 2H), 7.43–7.50 (PhH, m, 3H); Anal. Calcd
for C12H13N: C, 84.16; H, 7.65; N, 8.18. Found: C,
79.91; H, 7.50; N, 8.02.
2,5-Dimethylfuran: Colorless liquid; 1H NMR
(300 MHz, CDCl3) δH (ppm): 2.23 (CH3, s, 6H), 5.81
(furan, s, 2H); GC/MS (m/z): M+ 96, 81, 53, 43. Anal.
Calcd for C6H8O: C, 75.00; H, 8.33; O, 16.67. Found:
C, 74.96; H, 8.35; O, 16.70.
2,5-Dimethylthiophene: Liquid; 1H NMR (300
MHz, CDCl3) δH (ppm): 2.32 (CH3, s, 6H), 6.43 (thio-
phene, s, 2H); GC/MS (m/z): M+ 112, 111, 97, 77, 59,
45, 39, 27. Anal. Calcd for C6H8S: C, 64.29; H, 7.14;
S, 28.57. Found: C, 64.32; H, 7.12; S, 28.58.
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Heteroatom Chemistry DOI 10.1002/hc