518
A. Saeed et al. · Substituted Thiazol-2-ylidene-benzamides
2-Fluoro-N-(3-(3-fluorophenyl)-4-methylthiazol-2(3H)-ylid-
N-(3-(4-fluorophenyl)-4-methylthiazol-2(3H)-ylidene)-
ene)benzamide (34)
3,4,5-trimethoxybenzamide (37)
From 1-(4-fluorobenzoyl)-3-(3,4,5-trimethoxybenzoyl)-
thiourea (17) (364 mg). Yield: 381 mg (88 %), m. p. 180 ◦C. –
IR (cm−1): ν = 599 (C=O), 1498 (C=N). – 1H NMR
(CDCl3): δ = 7.39 – 7.35 (m, 4H, Ar-H); 7.28 (dt, 2H,J =
2.1, 8.3 Hz, Ar-H); 6.41 (q, 1H,J = 1.2 Hz, CH=C); 3.86
(s, 3H, OCH3); 3.79 (s, 6H, 2 × OCH3); 2.11 (d, 3H, J =
1.2 Hz, CH3). – 13C NMR (CDCl3): δ = 173.0 (C=O);
From 1-(3-fluorobenzoyl)-3-(2-fluorophenyl)thiourea (14)
(292 mg). Yield: 254 mg (87 %), m. p. 117 ◦C. – IR (cm−1):
ν = 609 (C=O), 1467 (C=N). – 1H NMR (CDCl3): δ =
7.31 – 7.69 (m, 8H, Ar-H); 6.43 (q, 1H, J = 1.2 Hz, CH=C);
2.12 (d, 3H, J = 1.2 Hz, CH3). – 13C NMR (CDCl3): δ =
173.3 (C=O); 169.6 (C=N); 162.4 (d, 1J = 256 Hz); 157.9
(d, 1JC,F = 251 Hz); 134.0, 132.6 (d, 3JC,F = 8.8 Hz); 132.2
(d, 4JC,F = 0.8 Hz); 131.1 (d, 3J = 9.0 Hz); 130.3, 125.1 (d,
1
169.9 (C=N); 162.6 (d, JC,F = 248 Hz); 152.5 (2C); 140.8,
4
3
3JC,F = 7.5 Hz); 124.6 (d, 4JC,F = 3.0 Hz); 123.3 (d, 4JC,F
=
134.1, 133.3 (d, JC,2F = 3.0 Hz); 132.1, 130.2 (d, JC,F
=
3.8 Hz); 116.9 (d, 2JC,F = 21.0 Hz); 116.6 (d, 2J = 22.5 Hz);
105.1 (CH=C); 15.0 (CH3). – MS (FAB): m/z = 330/332
[M+H]+. – C17H12F2N2OS: calcd. C 61.81, H 3.66, N 8.48;
found C 61.67, H 3.60, N 8.22.
8.3 Hz); 116.3 (d, JC,F = 23.0 Hz); 106.1 (2C); 104.5
(CH=C); 60.9 (OCH3); 55.77 (2C, 2 × OCH3); 15.0 (CH3). –
MS (FAB): m/z = 402/404 [M+H]+. – C20H19FN2O5S:
calcd. C 59.69, H 4.76, N 6.96; found C 59.39, H 4.68,
N 6.80.
N-(3-(3-fluorophenyl)-4-methylthiazol-2(3H)-ylidene)-
3,4,5-trimethoxybenzamide (35)
3-Fluoro-N-(3-(4-fluorophenyl)-4-methylthiazol-2(3H)-ylid-
ene)benzamide (38)
From 1-(3-fluorophenyl)-3-(3,4,5-trimethoxybenzoyl)-
From 1-(3-fluorobenzoyl)-3-(4-fluorophenyl)thiourea (18)
(292 mg). Yield: 271 mg (82 %), m. p. 174 ◦C. – IR
(cm−1): ν = 660 (C=O), 1467 (C=N). – 1H NMR (CDCl3):
δ = 7.39 – 7.35 (m, 4H, Ar-H); 7.28 (dt, 2H,J = 2.1,
8.3 Hz, Ar-H); 6.41 (q, 1H,J = 1.2 Hz, CH=C); 3.86 (s,
3H, OCH3); 3.79 (s, 6H, 2 × OCH3); 2.11 (d, 3H, J =
1.2 Hz, CH3). – 13C NMR (CDCl3): δ = 173.0 (C=O);
thiourea (15) (364 mg). Yield: 390 mg (90 %), m. p. 172
1
◦C. – IR (cm−1): ν = 613 (C=O), 1509 (C=N). – H NMR
(CDCl3): δ = 77.56 (q, 1H, J = 8.1 Hz, Ar-H); 7.37 (s,
2H, Ar-H); 7.29 – 7.20 (m, 1H, Ar-H); 7.14 (dt, 1H,J =
2.1, 8.1 Hz, Ar-H); 6.42 (q, 1H,J = 1.2 Hz, CH=C); 3.87
(s, 3H, OCH3); 3.67 (s, 6H, 2 × OCH3); 2.10 (d, 3H, J =
1.2 Hz, CH3). – 13C NMR (CDCl3): δ = 172.4 (C=O);
1
169.9 (C=N); 162.6 (d, JC,F = 248 Hz); 152.5 (2C); 140.8,
1
169.5 (C=N); 162.7 (d, JC,F = 247 Hz); 152.5 (2C); 140.7,
4
3
134.1, 133.3 (d, JC,2F = 3.0 Hz); 132.1, 130.2 (d, JC,F
=
3
3
138.6 (d, JC,F = 9.75 Hz); 133.9, 132.0, 130.5 (d, JC,F
=
=
8.3 Hz); 116.3 (d, JC,F = 23.0 Hz); 106.1 (2C); 104.5
(CH=C); 60.9 (OCH3); 55.77 (2C, 2 × OCH3); 15.0 (CH3). –
MS (FAB): m/z = 402/404 [M+H]+. – C17H12F2N2OS:
calcd. C 61.81, H 3.66, N 8.48; found C 61.60, H 3.60,
N 8.27.
4
2
8.25 Hz), 123.9 (d, JC,F = 3.8 Hz); 116.5 (d, JC,F
2
21.5 Hz); 115.2 (d, JC,F = 22.5 Hz); 106.2 (2C); 104.3
(CH=C); 60.7 (OCH3); 55.7 (2C, 2 × OCH3); 14.2 (CH3). –
MS (FAB): m/z = 402/404 [M+H]+. – C20H19FN2O5S:
calcd. C 59.69, H 4.76, N 6.96; found C 59.37, H 4.64,
N 6.75.
N-(3-(3-Chloro-4-fluorophenyl)-4-methylthiazol-2(3H)-ylid-
ene)-3,4,5-trimethoxybenzamide (39)
3-Fluoro-N-(3-(3-fluorophenyl)-4-methylthiazol-2(3H)-ylid-
From 1-(3-chloro-4-fluorophenyl)-3-(3,4,5-trimethoxy-
ene)benzamide (36)
benzoyl)thiourea (19) (400 mg). Yield: 376 mg (86 %),
◦
From 1-3-fluorobenzoyl)-3-(3-fluorophenyl)thiourea (16) m. p. 137 C. – IR (cm−1): ν = 608 (C=O), 1543 (C=N). –
(400 mg). Yield: 261 mg (79 %), m. p. 166 ◦C. – IR (cm−1): 1H NMR (CDCl3): δ = 7.57 (dd, 1H, J = 2.7, 6.3 Hz,
ν = 605 (C=O), 1588 (C=N). – 1H NMR (CDCl3): δ = Ar-H); 7.39 – 7.24 (m, 4H, Ar-H); 6.42 (q, 1H, J = 1.2 Hz,
77.68 – 7.26 (m, 8H, Ar-H); 6.43 (q, 1H, J = 0.9 Hz, CH=C); CH=C); 3.87 (s, 3H, OCH3); 3.82 (s, 6H, 2 × OCH3);
2.11 (d, 3H, J = 0.9 Hz, CH3). – 13C NMR (CDCl3): δ = 2.14 (d, 3H, J = 1.2 Hz, CH3). – 13C NMR (CDCl3): δ =
1
173.7 (C=O); 169.2 (C=N); 162.6 (d, 1JC,F = 257 Hz); 157.9 173.6 (C=O); 169.9 (C=N); 158.2 (d, JC,F = 251 Hz);
4
(d, 1JC,F = 257 Hz); 134.1, 132.5 (d, 3JC,F = 8.8 Hz); 132.1 152.6 (2C); 140.9, 133.6 (d, JC,F = 3.8 Hz); 133.5, 131.8,
(d, 4JC,F = 3.75 Hz); 131.2 (d, 3JC,F = 8.8 Hz); 130.4, 125.2 131.0, 128.2 (d, 3JC,F = 7.5 Hz); 121.8 (d, 2JC,F = 18.8 Hz);
3
4
2
(d, JC,F = 8.8 Hz); 124.7 (d, JC,F = 0.8 Hz); 123.4 (d, 117.1 (d, JC,F = 21.7 Hz); 106.1 (2C); 104.8 (CH=C);
4JC,F = 3 Hz); 116.9 (d, JC,F = 18.8 Hz); 116.6 (d, JC,F
=
60.9 (OCH3); 55.8 (2C, 2 × OCH3); 15.0 (CH3). – MS
2
2
21.0 Hz); 104.8 (CH=C); 15.0 (CH3). – MS (FAB): m/z = (FAB): m/z = 436/438 [M+H]+. – C20H18ClFN2O4S:
330/332 [M+H]+. – C17H22FN2O5S: calcd. C 61.81, H 3.66, calcd. C 54.98, H 4.15, N 6.41; found C 54.77, H 4.03,
N 8.48; found C 61.63, H 3.59, N 8.29.
N 6.20.
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