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Med Chem Res (2011) 20:29–35
6-[3-(Diethylamino)propoxyl]benzo[d][1,3]oxathiol-2-
one 5c
then washed with water and dried overnight on anhydrous
sodium sulfate. Methylene dichloride was removed under
vacuum to afford residue. The residue was recrystallized
from ethanol to furnish 4.
Yield: 2.92 g (52%), mp: 84°C, molecular formula:
C14H17NO4S (281), elemental analysis: calcd. C 59.76, H
6.81, N 4.98, O 17.06, S 11.40; found C 59.68, H 6.77, N
4.81, O 17.38, S 11.36. IR mmax (cm-1) (KBr): 3073, 2941,
Yield: 2.63 g (63%), mp: 74°C, molecular formula:
C10H9ClO3S (244), elemental analysis: calcd. C 49.08, H
3.71, Cl 14.49, O 19.62, S 13.10; found C 49.28, H 3.59, Cl
14.41, O 19.43, S 13.23. IR mmax (cm-1) (KBr): 3040,
1
1710, 1406. H NMR (d ppm, DMSO d6): 6.81(s, 1H, C7–
1
H), 6.71 (d, 2H, C4–H, and C5–H), 4.15 (t, 2H, –OCH2),
3.81 (t, 2H, –CH2CH2N–), 3.72 (q, 4H, NCH2–), 2.87 (m,
2H, –CH2–), 1.6(t, 6H –CH3).
2979, 1734, 1471, 1150, 1035. H NMR (d ppm; CDCl3):
6.8 (s, 1H, C7–H), 6.73 (d, 2H, C4–H, and C5–H), 4.15 (t,
2H, –OCH2), 3.80 (t, 2H, –CH2Cl), 2.24 (m, 2H, –CH2–).
General method of synthesis for compounds 5a–5e
6-[3-(Piperazin-1-yl)propoxyl]benzo[d][1,3]oxathiol-2-
one 5d
A mixture of 4 (4.88 g, 0.02 mol), appropriate sec amine
(0.02 mol) and anhydrous K2CO3 (3.50 g, 0.025 mol) was
added to the reaction flask and refluxed in acetonitrile for
18 h. The reaction mixture was filtered and the filtrate was
concentrated under vacuum. The residue was dissolved in
methylene dichloride. The solution was washed with water
and then with 10% HCl. The organic layer was then
washed again with water and dried overnight on anhydrous
sodium sulfate. Methylene dichloride was removed under
vacuum to afford residue. The residue was then recrystal-
lised from ethanol–water to yield the desired compound.
Yield: 3.82 g (65%), mp: 126°C, molecular formula:
C14H18N2O3S (294), elemental analysis: calcd. C 57.12, H
6.16, N 9.52, O 16.31, S 10.89; found C 57.08, H 6.12, N
9.47, O 16.47, S 10.86. IR mmax (cm-1) (KBr): 3290, 3018,
2964, 1720, 1587, 1410. H NMR (d, ppm, DMSO d6):
9.36 (s, 1H, NH), 6.81(s, 1H, C7–H), 6.71 (d, 2H, C4–H,
1
and C5–H), 4.15 (0t, 2H, –OCH2), 3.84 (t, 2H, –CH2CH2N–
0
0
), 3.75 (m, 4H C2 –H, and C6 –H), 3.73(m, 4H C3 –H, and
0
C5 –H), 2.87 (m, 2H, –CH2–).
6-[3-(4H-1,2,4-Triazol-4-yl)propoxyl]benzo[d][1,3]
oxathiol-2-one 5e
6-[3-(Piperidin-1-yl)propoxyl]benzo[d][1,3]oxathiol-2-
one 5a
Yield: 3.21 g (58%), mp: 133°C, molecular formula
C12H11N3O3S (277), elemental analysis: calcd. C 51.98, H
4.00, N 15.15, O 17.31, S 11.56; found C 51.91, H 3.86, N
15.11, O 17.63, S 11.49. IR mmax (cm-1) (KBr): 3080,
2964, 1728, 1427, 1392,1379, 1188. 1H NMR (d ppm,
DMSO d6): 6.80 (s, 1H, C7–H), 6.73 (d, 2H, C4–H, and
C5–H), 4.15 (t, 2H, –OCH2), 3.86 (t, 2H, –CH2N), 3.25 (s,
Yield: 3.28 g (56%), mp: 92°C, molecular formula:
C15H19NO3S (293), elemental analysis: calcd. C 61.41, H
6.53, N 4.77, O 16.36, S 10.93, found C 61.27, H 6.78, N
4.69, O 16.48, S 10.78. IR mmax (cm-1) (KBr): 3017, 2941,
1720, 1423, 1150, 1045. H NMR (d ppm; DMSO-d6):
6.81(s, 1H, C7–H), 6.73 (d, 2H, C4–H, and C5–H), 4.16 (t,
1
2H, –OCH2–), 3.89 (t, 2H, –CH2CH2N–), 1.63 (m, 6H,
0
0
0
0
0
0
0
2H, C3 –H, and C5 –H), 2.85 (m, 2H, –CH2–).
C3 –H, C4 –H, C5 –H), 2.65 (t, 4H, C2 –H, and C6 –H), 2.85
(m, 2H, –CH2–).
General method of synthesis of compounds 5f–5j
6-[3-(Morpholin-4-yl)propoxyl]benzo[d][1,3]oxathiol-2-
one 5b
A mixture of 4 (4.88 g, 0.02 mol), appropriate phenol
(0.02 mol), and anhydrous K2CO3 (3.50 g, 0.025 mol) was
refluxed in acetonitrile for 36 h. The reaction mixture was
filtered and concentrated under vacuum, residue dissolved
in methylene dichloride and washed with water and then
with 5% NaOH. Organic layer was again washed with
water and dried over anhydrous sodium sulfate. The filtrate
was concentrated under vacuum to provide crude solid. It
was than recrystallised from absolute ethanol to yield
desired compound.
Yield: 3.24 g (55%), mp: 98°C, molecular formula:
C14H17NO4S (295), elemental analysis: calcd. C 56.93, H
5.80, N 4.74, O 21.67, S 10.86; found. C 57.09, H 5.91, N
4.67, O 21.67, S 10.66. IR mmax (cm-1) (KBr): 3006, 2953,
1734, 1440, 1355, 1045. H NMR (d ppm; DMSO-d6):
6.81(s, 1H, C7–H), 6.73 (d, 2H, C4–H, and C5–H), 4.15 (t,
1
0
0
2H, –OCH2–), 4.02 (t, 4H, C2 –H, and C6 –H), 3.87 (t, 2H,
0
0
–CH2CH2N–), 3.81 (t, 4H, C3 –H, and C5 –H), 2.85 (m,
2H, –CH2–).
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