V. Alagarsamy, M. Senthilraja, and V. Raja Solomon
Vol 000
Synthesis of N-4-(4-chlorophenyl)-thiazol-2-yl-chloroacetamide
0.01mol) were taken in a 100-mL round bottom flask. The
solution was stirred vigorously and reflux for 3 h. After the
completion of the reaction, the solution was evaporated to
dryness. The solid obtained was washed with water and
dried. The residue was recrystallized with methanol.
(7). Yield 65%, mp 204–206ꢂC; IR (KBr, cmꢀ1): 3431
(NH), 3056 (Ar─CH), 2915 (CH2), 1705 (C═O), 736
1
(CH2─Cl). H-NMR (CDCl3) d (ppm): 4.27 (s, 2H, CH2),
6.64 (s, 1H, CH), 7.33 (d, J = 7.5 Hz, 2H, Ar─H), 7.42
(d, J = 8.0 Hz, 2H, Ar─H), 8.20 (br s, 1H, NH). MS (m/z):
287 [M+]. Anal. Calcd for C11H8 Cl2N2 OS: C, 46.01; H,
2.81; N, 9.76. Found: C, 46.19; H, 2.80; N, 9.72.
Synthesis of 3-(4-(4-chlorophenyl)-thiazol-2-yl)-2-iminothiazolidin-
4-one (13). Yield 63%, mp 186–188ꢂC; IR (KBr, cmꢀ1): 3425
(NH), 3057 (Ar─CH), 1626 (C═NH), 1715 (C═O), 735
1
Synthesis of N-4-(4-bromophenyl)-thiazol-2-yl-chloroacetamide
(C─Cl). H-NMR (CDCl3) d (ppm): 3.76 (s, 2H, CH2), 6.65
(8).
Yield 58%, mp 178–180ꢂC; IR (KBr, cmꢀ1): 3412
(s, 2H, CH), 7.33–7.42 (d, 4H, Ar─H), 10.5 (br s, 1H, NH).
MS (m/z): 309 [M+]. Anal. Calcd for C12H8 ClN3 OS2: C,
(NH), 3073 (Ar─CH), 2933 (CH2), 1712 (C═O), 622
1
(C─Br), 745 (CH2─Cl). H-NMR (CDCl3) d (ppm): 4.21
46.52; H, 2.60; N, 13.56. Found: C, 46.70; H, 2.59; N, 13.51.
Synthesis of 3-(4-(4-bromophenyl)-thiazol-2-yl)-2-iminothiazolidin-
4-one (14). Yield 70%, mp 153–155ꢂC; IR (KBr, cmꢀ1):
3436 (NH), 3042 (Ar─CH), 1620 (C═NH), 1712 (C═O),
648 (C─Br). 1H-NMR (CDCl3) d (ppm): 3.74 (s, 2H, CH2),
6.62 (s, 1H, CH), 7.37 (d, J= 8.0 Hz, 2H, Ar─H), 7.49 (d,
J= 8.0 Hz, 2H, Ar─H), 10.8 (br s, 1H, NH). MS (m/z): 354
[M+]. Anal. Calcd for C12H8 BrN3OS2: C, 40.69; H, 2.28; N,
11.86. Found: C, 40.85; H, 2.27; N, 11.82.
(s, 2H, CH2), 6.60 (s, 1H, CH), 7.37 (d, J=7.5Hz, 2H,
Ar─H), 7.49 (d, J= 8.0 Hz, 2H, Ar─H), 8.03 (br s, 1H, NH).
MS (m/z): 331 [M+]. Anal. Calcd for C11H8 BrClN2OS: C,
39.84; H, 2.43; N, 8.45. Found: C, 39.68; H, 2.44; N, 8.48.
Synthesis
chloroacetamide (9).
of
N-4-(4-hydroxyphenyl)-thiazol-2-yl-
Yield 66%, mp 196–198ꢂC; IR
(KBr, cmꢀ1): 3510 (OH), 3423 (NH), 3073 (Ar─CH),
2953 (CH2), 1708 (C═O), 728 (CH2─Cl). 1H-NMR
(CDCl3) d (ppm): 4.28 (s, 2H, CH2), 5.02 (s, 1H, Ar─OH),
6.62 (s, 1H, CH), 6.79 (d, J = 7.5 Hz, 2H, Ar─H), 7.31
(d, J = 7.5 Hz, 2H, Ar─H), 8.16 (br s, 1H, NH). MS (m/z):
268 [M+]. Anal. Calcd for C11H9 ClN2O2S: C, 49.17; H,
3.38; N, 10.42. Found: C, 49.36; H, 3.37; N, 10.38.
Synthesis of 3-(4-(4-hydroxyphenyl)-thiazol-2-yl)-2-iminothiazolidin-
4-one (15). Yield 72%, mp 166–168ꢂC; IR (KBr, cmꢀ1):
3526(OH), 3412 (NH), 3053 (Ar─CH), 1612 (C═NH),
1696 (C═O). 1H-NMR (CDCl3) d (ppm): 3.76 (s, 2H, CH2),
5.08 (s, Ar─OH), 6.67 (s, 1H, CH), 6.79 (d, J=7.0Hz, 2H,
Ar─H), 7.31 (d, J= 7.5 Hz, 2H, Ar─H), 10.8 (br s, 1H,
NH). MS (m/z): 291 [M+]. Anal. Calcd for C12H9 N3O2S2:
C, 49.47; H, 3.11; N, 14.42. Found: C, 49.27; H, 3.12; N,
14.48.
Synthesis of N-4-(4-fluorophenyl)-thiazol-2-yl-chloroacetamide
(10). Yield 71%, mp 205–207ꢂC; IR (KBr, cmꢀ1): 3419
(NH), 3056 (Ar─CH), 2912 (CH2), 1708 (C═O), 1056
1
(C─F), 720 (CH2─Cl). H-NMR (CDCl3) d (ppm): 4.25
(s, 2H, CH2), 6.62 (s, 1H, CH), 7.03 (d, J=8.0Hz, 2H,
Ar─H), 7.46 (d, J= 8.0 Hz, 2H, Ar─H), 8.06 (br s, 1H, NH).
MS (m/z): 270 [M+]. Anal. Calcd for C11H8 Cl FN2 OS: C,
48.80; H, 2.98; N, 10.35. Found: C, 48.99; H, 2.97; N, 10.31.
Synthesis of 3-(4-(4-fluorophenyl)-thiazol-2-yl)-2-iminothiazolidin-
4-one (16). Yield 68%, mp 226–228ꢂC; IR (KBr, cmꢀ1):
3432 (NH), 3062 (Ar─CH), 1619 (C═NH), 1705 (C═O),
1049 (C─F). 1H-NMR (CDCl3) d (ppm): 3.75 (s, 2H,
CH2), 6.68 (s, 1H, CH), 7.03 (d, J= 7.5 Hz, 2H, Ar─H),
7.46 (d, J= 7.5 Hz, 2H, Ar─H), 11.0 (br s, 1H, NH);
13C-NMR (CDCl3) d (ppm): 24.51, 97.89, 114.58, 127.25,
128.53, 146.25, 159.53, 161.39, 170.89, 172.54; MS (m/z):
293 [M+]. Anal. Calcd for C12H8 FN3 OS2: C, 49.13; H,
2.75; N, 14.32. Found: C, 49.32; H, 2.74; N, 14.26.
Synthesis of N-4-(4-aminophenyl)-thiazol-2-yl-chloroacetamide
(11). Yield 72%, mp 232–234ꢂC; IR (KBr, cmꢀ1): 3416
(NH), 3248 (NH2), 3052 (Ar─CH), 2920 (CH2), 1710
1
(C═O), 722 (CH2─Cl). H-NMR (CDCl3) d (ppm): 4.00
(s, 2H, NH2), 4.27 (s, 2H, CH2), 6.63 (s, 1H, CH), 6.52
(d, J= 7.5 Hz, 2H, Ar─H), 7.23 (d, J= 8.0 Hz, 2H, Ar─H),
8.06 (br s, 1H, NH). MS (m/z): 267 [M+]. Anal. Calcd for
C11H10 ClN3O S: C, 49.35; H, 3.76; N, 15.69. Found: C,
Synthesis of 3-(4-(4-aminophenyl)-thiazol-2-yl)-2-iminothiazolidin-
4-one (17). Yield 70%, mp 257–259ꢂC; IR (KBr, cmꢀ1):
49.15; H, 3.78; N, 15.75.
3456 (NH), 3291 and 3246 (NH2), 3042 (Ar─CH), 1614
1
Synthesis of N-4-(4-methoxyphenyl)-thiazol-2-yl-chloroacetamide
(C═NH), 1710 (C═O), H-NMR (CDCl3) d (ppm): 3.78
(12). Yield 69%, mp 212–214ꢂC; IR (KBr, cmꢀ1): 3420
(s, 2H, CH2), 4.08 (s, 2H, NH2), 6.65 (s, 1H, CH), 6.52
(d, J= 8.0 Hz, 2H, Ar─H), 7.23 (d, J= 8.0 Hz, 2H, Ar─H),
10.3 (br s, 1H, NH). MS (m/z): 267 [M+]. Anal. Calcd
for C12H10 N4O S2: C, 49.64; H, 3.47; N, 19.30. Found:
(NH), 3048 (Ar─CH), 2916 (CH2), 2820 (OCH3), 1706
(C═O), 730 (CH2-Cl). 1H-NMR (CDCl3) d (ppm): 3.73
(s, 3H, OCH3), 4.27 (s, 2H, CH2), 6.64 (s, 1H, CH), 6.83
(d, J= 7.5 Hz, 2H, Ar─H), 7.37 (d, J=7.5Hz, 2H, Ar─H),
8.04 (br s, 1H, NH). MS (m/z): 282 [M+]. Anal. Calcd for
C12H11 Cl N2 O2 S: C, 50.97; H, 3.92; N, 9.91. Found: C,
51.17; H, 3.90; N, 9.87.
C, 49.83; H, 3.46; N, 19.22.
Synthesis of 3-(4-(4-methoxyphenyl)-thiazol-2-yl)-2-iminothiazolidin-
4-one (18). Yield 72%, mp 242–244ꢂC; IR (KBr, cmꢀ1):
3422 (NH), 3052 (Ar─CH), 2818 (OCH3), 1716 (C═O),
1
1616 (C═NH). H-NMR (CDCl3) d (ppm): 3.73 (s, 3H,
General procedure for synthesis of 3-substituted-thiazolyl-
2-iminothiazolidin-4-ones (13–18).
A solution of 4-
OCH3), 3.76 (s, 2H, CH2), 6.68 (s, 1H, CH), 6.83
(d, J = 8.0 Hz, 2H, Ar─H), 7.37 (d, J = 7.5 Hz, 2H, Ar─H),
10.6 (br s, 1H, NH). MS (m/z): 282 [M+]. Anal. Calcd for
substituted-thiazol-2-yl-chloroacetamides (7–12) (0.01mol)
in acetone (50 mL) and potassium thiocyanide (0.6 g,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet