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4.2.2.7. Compound IIIl. 1H NMR (CDCl3), d: 2.31 (s, 3H,
CH3), 3.21 (dd, 1H, HA, JA–B = 16.34 Hz, JA–X = 9.28 Hz),
3.77 (dd, HB, JA–B = 16.34 Hz, JB–X = 8.34 Hz), 4.18 (dd, HX,
4.2.2.14. Compound Vf. 1H NMR (CDCl3), d: 1.18 (t, 3H, –
O–CH2–CH3), 2.48 (s, 3H, CH3), 3.11 (dd, 1H, HA, JA–
B = 16.31 Hz, JA–X = 9.31 Hz), 3.77 (dd, HB, JA–B = 16.31 Hz,
JA–X = 9.28 Hz, JB–X = 8.34 Hz), 6.71–7.79 (m, 6H, Ar-H),
JB–X = 8.41 Hz), 4.01 (q, 2H, –O–CH2–CH3), 4.12 (dd, HX, JA–
8.23 (bs, 1H, COOH). IR (cmÀ1): 1680 (C O), 3277 (bs-OH),
1128 (C–F). Anal. Calcd. for C18H13F4NO2S: C, 56.39; N, 3.65.
Found: C, 56.56; N, 3.64.
X = 9.31 Hz, JB–X = 8.41 Hz), 4.98 (s, 1H, Cl–CH), 6.63–7.82
(m, 6H, Ar-H), 8.19 (bs, 1H, COOH). IR (cmÀ1): 1685, 1728
(two C O), 3275 (bs-OH), 1145 (C–F), 745 (C–Cl). Anal.
Calcd. for C21H19ClFNO4S: C, 57.86; N, 3.21. Found: C, 57.67;
N, 3.22.
4.2.2.8. Compound IIIm. 1H NMR (CDCl3), d: 2.37 (s, 3H,
CH3), 2.41 (s, 3H, CH3), 3.22 (dd, 1H, HA, JA–B = 16.32 Hz, JA–
X = 9.28 Hz), 3.78 (dd, HB, JA–B = 16.32 Hz, JB–X = 8.32 Hz),
4.12 (dd, HX, JA–X = 9.28 Hz, JB–X = 8.32 Hz), 6.71–7.79 (m,
6H, Ar-H), 8.26 (bs, 1H, COOH). IR (cmÀ1): 1689 (C O), 3278
(bs-OH), 1130 (C–F). Anal. Calcd. for C19H16F3NO2S: C,
60.15; N, 3.69. Found: C, 60.32; N, 3.70.
4.2.2.15. Compound Vg. 1H NMR (CDCl3), d: 1.20 (t, 3H, –
CH2–CH3), 2.35 (s, 3H, CH3), 2.59 (q, 2H –CH2–CH3), 3.16
(dd, 1H, HA, JA–B = 16.27 Hz, JA–X = 9.29 Hz), 3.71 (dd, HB,
JA–B = 16.27 Hz, JB–X = 8.42 Hz), 4.11 (dd, HX, JA–
X = 9.29 Hz, JB–X = 8.42 Hz), 4.95 (s, 1H, Cl–CH), 6.62–
7.81 (m, 7H, Ar-H), 8.21 (bs, 1H, COOH). IR (cmÀ1): 1688,
1725 (two C O), 3278 (bs-OH), 1142 (C–F), 748 (C–Cl). Anal.
Calcd. for C19H15ClFNO3S: C, 55.95; N, 3.43. Found: C, 55.80;
N, 3.42.
4.2.2.9. Compound Va. 1H NMR (CDCl3), d: 2.31 (s, 3H,
CH3), 3.14 (dd, 1H, HA, JA–B = 16.31 Hz, JA–X = 9.26 Hz),
3.76 (dd, HB, JA–B = 16.31 Hz, JB–X = 8.41 Hz), 4.13 (dd, HX,
J
A–X = 9.26 Hz, JB–X = 8.41 Hz), 4.98 (s, 1H, Cl–CH), 6.67–
7.85 (m, 7H, Ar-H), 8.16 (bs, 1H, COOH). IR (cmÀ1): 1680,
1738 (two C O), 3270 (bs, OH), 1140 (C–F), 740 (C–Cl). Anal.
Calcd. for C19H15ClFNO3S: C, 58.24; N, 3.57. Found: C, 58.09;
N, 3.58.
4.2.2.16. Compound Vh. 1H NMR (CDCl3), d: 3.18 (dd, 1H,
HA, JA–B = 16.32 Hz, JA–X = 9.31 Hz), 3.72 (dd, HB, JA–
B = 16.32 Hz, JB–X = 8.40 Hz), 4.18 (dd, HX, JA–X = 9.31 Hz,
J
B–X = 8.40 Hz), 5.02 (s, 1H, Cl–CH), 6.62–7.84 (m, 7H, Ar-
H), 8.18 (bs, 1H, COOH). IR (cmÀ1): 1692, 1720 (two C O),
3275 (bs-OH), 1135 (C–F), 742 (C–Cl). Anal. Calcd. for
C19H12Cl2F3NO3S: C, 49.37; N, 3.03. Found: C, 49.53; N, 3.02.
4.2.2.10. Compound Vb. 1H NMR (CDCl3), d: 3.18 (dd, 1H,
HA, JA–B = 16.32 Hz, JA–X = 9.27 Hz), 3.72 (dd, HB, JA–
B = 16.32 Hz, JB–X = 8.40 Hz), 4.12 (dd, HX, JA–X = 9.27 Hz,
J
B–X = 8.40 Hz), 4.97 (s, 1H, Cl–CH), 6.68–7.84 (m, 7H, Ar-
4.2.2.17. Compound Vi. 1H NMR (CDCl3), d: 3.22 (dd, 1H,
HA, JA–B = 16.30 Hz, JA–X = 9.28 Hz), 3.71 (dd, HB, JA–
B = 16.30 Hz, JB–X = 8.39 Hz), 4.20 (dd, HX, JA–X = 9.28 Hz,
H), 8.15 (bs, 1H, COOH). IR (cmÀ1): 1695, 1726 (two C O),
3270 (bs, OH), 1146 (C–F), 735 (C–Cl). Anal. Calcd. for
C18H12ClF2NO3S: C, 54.62; N, 3.54. Found: C, 54.80; N, 3.55.
J
B–X = 8.39 Hz), 4.98 (s, 1H, Cl–CH), 6.65–7.82 (m, 7H, Ar-
H), 8.12 (bs, 1H, COOH). IR (cmÀ1): 1685, 1722 (two C O),
3270 (bs-OH), 1142 (C–F), 740 (C–Cl). Anal. Calcd. for
C19H12BrClF3NO3S: C, 45.04; N, 2.76. Found: C, 45.19; N,
2.75.
4.2.2.11. Compound Vc. 1H NMR (CDCl3), d: 3.15 (dd, 1H,
HA, JA–B = 16.28 Hz, JA–X = 9.30 Hz), 3.75 (dd, HB, JA–
B = 16.28 Hz, JB–X = 8.42 Hz), 4.16 (dd, HX, JA–X = 9.30 Hz,
J
B–X = 8.42 Hz), 5.01 (s, 1H, Cl–CH), 6.68–7.85 (m, 7H, Ar-
H), 8.17 (bs, 1H, COOH). IR (cmÀ1): 1690, 1725 (two C O),
3275 (bs, OH), 1142 (C–F), 750 (C–Cl). Anal. Calcd. for
C18H12Cl2NO3S: C, 52.44; N, 3.40. Found: C, 52.60; N, 3.42.
4.2.2.18. Compound Vj. 1H NMR (CDCl3), d: 3.18 (dd, 1H,
HA, JA–B = 16.34 Hz, JA–X = 9.26 Hz), 3.68 (dd, HB, JA–
B = 16.34 Hz, JB–X = 8.38 Hz), 4.24 (dd, HX, JA–X = 9.26 Hz,
J
B–X = 8.38 Hz), 4.96 (s, 1H, Cl–CH), 6.62–7.81 (m, 7H, Ar-
4.2.2.12. Compound Vd. 1H NMR (CDCl3), d: 3.16 (dd, 1H,
HA, JA–B = 16.30 Hz, JA–X = 9.33 Hz), 3.77 (dd, HB, JA–
B = 16.30 Hz, JB–X = 8.38 Hz), 4.19 (dd, HX, JA–X = 9.33 Hz,
H), 8.08 (s, 1H, OH), 8.26 (bs, 1H, COOH). IR (cmÀ1): 1670,
1728 (two C O), 3265 (bs-OH), 1160 (C–O), 1120 (C–F), 730
(C–Cl). Anal. Calcd. for C19H13ClF3NO4S: C, 51.42; N, 3.16.
Found: C, 51.59; N, 3.17.
JB–X = 8.38 Hz), 4.99 (s, 1H, Cl–CH), 6.65–7.80 (m, 7H, Ar-H),
8.15 (bs, 1H, COOH). IR (cmÀ1): 1698, 1729 (two C O), 3265
(bs, OH), 1148 (C–F), 735 (C–Cl). Anal. Calcd. for
C18H12BrClFNO3S: C, 47.34; N, 3.07. Found: C, 47.18; N, 3.08.
4.2.2.19. Compound Vk. 1H NMR (CDCl3), d: 3.21 (dd, 1H,
HA, JA–B = 16.27 Hz, JA–X = 9.29 Hz), 3.69 (dd, HB, JA–
B = 16.27 Hz, JB–X = 8.38 Hz), 4.16 (dd, HX, JA–X = 9.29 Hz,
4.2.2.13. Compound Ve. 1H NMR (CDCl3), d: 3.19 (dd, 1H,
HA, JA–B = 16.33 Hz, JA–X = 9.35 Hz), 3.71 (dd, HB, JA–
B = 16.33 Hz, JB–X = 8.37 Hz), 3.73 (s, 3H, OCH3), 4.20 (dd,
HX, JA–X = 9.35 Hz, JB–X = 8.37 Hz), 5.03 (s, 1H, Cl–CH),
6.67–7.83 (m, 7H, Ar-H), 8.22 (bs, 1H, COOH). IR (cmÀ1):
1690, 1730 (two C O), 3270 (bs-OH), 1140 (C–F), 740 (C–Cl).
Anal. Calcd. for C19H15ClFNO4S: C, 55.95; N, 3.43. Found: C,
55.76; N, 3.44.
JB–X = 8.38 Hz), 5.02 (s, 1H, Cl–CH), 6.66–7.86 (m, 6H, Ar-
H), 8.16 (bs, 1H, COOH). IR (cmÀ1): 1680, 1720 (two C O),
3260 (bs-OH), 1125 (C–F), 740 (C–Cl). Anal. Calcd. for
C18H11Cl3FNO3S: C, 48.40; N, 3.14. Found: C, 48.56; N, 3.15.
4.2.2.20. Compound Vl. 1H NMR (CDCl3), d: 2.35 (s, 3H,
CH3), 3.20 (dd, 1H, HA, JA–B = 16.20 Hz, JA–X = 9.33 Hz),
3.74 (dd, HB, JA–B = 16.20 Hz, JB–X = 8.40 Hz), 4.22 (dd, HX,