13C (DMSO) d = 154.8, 141.5, 137.3, 132.6, 129.6, 125.0, 121.9,
116.3, 114.6, 34.2. HR-MS ESI positive mode: m/z: calcd for
for hosting him as guest assistant professor. We also thank Dr
Girish Koripelly for carefully proof-reading this manuscript.
+
C10H11N2 159.092; found 159.094.
15 2-Naphthylamine (1 g, 6.98 mmol) and sodium thiocyanate
(1.13 g, 13.96 mmol) were dissolved in methanol (60 mL) at rt
and the pale yellow/brown solution was cooled to ꢂ25 1C. Bromine
(0.3 mL, 5.82 mmol) was addeddropwise and the reaction mixture
was stirred below ꢂ10 1C for 2 h. The pink suspension was then
warmed up to rt and 400 mL of water was added. The solid was
then collected by filtration under vacuum, washed with water and
dried under vacuum. To this pale yellow solid were added ethanol
(40 mL) and 1.5 M HCl (50 mL) and the suspension was refluxed
for 2 h. The hot suspension was then filtered under vacuum and the
filtrate was neutralized with K2CO3 at 0 1C until reaching pH
7–8. The aqueous solution was then extracted with CH2Cl2
(3 ꢁ 30 mL), the organic layers were dried over Na2SO4, filtered
and concentrated under vacuum to giving the desired naphtha-
[2,1-d]thiazol-2-amine as a brown powder (700 mg, 60%). To a
solution of naphtha[2,1-d]thiazol-2-amine (700 mg, 3.49 mmol)
in a mixture of acetonitrile (15 mL) and methanol (8 mL) was
added iodomethane (2 mL) and the reaction mixture was stirred
for 1 h at 45 1C. After evaporation under vacuum, the residue was
triturated in acetonitrile. The solid was then filtered off solution,
and was washed 3 times with hot acetonitrile and then with diethyl
ether. The desired N-methyl-2-amino-naphthathiazolium iodide
was thus obtained pure as a yellow solid (901 mg, 75%). NMR
1H (DMSO) d = 10.14 (s broad, 2H); 8.21 (d, J = 8.1 Hz, 1H);
8.15 (d, J = 8.1 Hz, 1H); 8.07 (d, J = 8.1 Hz, 1H); 7.93 (d, J =
8.9 Hz, 1H); 7.75 (t, J = 8.1 Hz, 1H); 7.66 (t, J = 7.9 Hz, 1H); 3.86
(s,3H). NMR 13C (DMSO) d = 167.4, 136.6, 130.2, 129.1, 128.9,
128.4, 126.4, 123.5, 123.0, 117.8, 113.4, 32.7. HR-MS ESI positive
mode: m/z: calcd for C12H11N2S+ 215.066; found 215.066.
16 K. Meguellati, M. Spichty and S. Ladame, Org. Lett., 2009, 11,
1123.
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14 2-Aminoquinoline (1 g, 6.93 mmol, purchased from TCI Europe)
was dissolved in a mixture of acetonitrile (40 mL) and iodomethane
(2 mL). The solution was stirred for 14 h at 45 1C. The
iodomethane was then evaporated off and the suspension was
filtered under vacuum. The white precipitate was then washed with
acetonitrile and diethyl ether, thus leading to the desired N-methyl-
2-amino-quinolinium iodide as an amorphous white solid (1.68 g,
75%). NMR 1H (DMSO) d = 9.11 (s broad, 2H); 8.36 (d, J = 9.3
Hz, 1H); 8 (t, J = 7.7 Hz, 2H); 7.88 (t, J = 7.7 Hz, 1H); 7.58
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ꢀc
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