Journal of Sulfur Chemistry 481
4.2.5. 4-Methoxy-N-(5-propyl-1,3-oxathiolan-2-ylidene)benzenamine (3e)
Pale yellow powder, yield: 0.44 g (87%). IR (KBr) (νmax/cm−1): 1631, 1592, 1367, 1173,
1
3
1082 cm−1. H NMR (500 MHz, CDCl3): δ = 1.11 (t, 3 H, J = 7.4, Me), 1.77–1.82 (m, 2 H,
CH2), 1.93–1.99 (m, 2 H, CH2), 3.08–3.12 (m, 1 H, CH), 3.34–3.37 (m, 1 H, CH), 3.81 (s, 3 H,
MeO), 4.52–4.55 (m, 1 H, CH), 6.85 (d, 2 H, 3J = 8.2, 2 CH), 6.92 (d, 2 H, 3J = 8.2, 2 CH). 13
C
NMR (125.7 MHz, CDCl3): δ = 10.8 (Me), 28.1 (CH2), 30.4 (CH2), 36.9 (CH2), 56.4 (MeO),
84.5 (CH), 115.2 (2 CH), 123.6 (2 CH), 143.3 (C), 157.3 (C), 164.3 (C). EI-MS: 358 (M+, 15),
327 (54), 300 (47), 281 (68), 77 (100), 31 (62). Anal. Calcd (%) for C13H17NO2S (251.34): C,
62.12, H, 6.82, N, 5.57. Found: C, 61.97, H, 6.73, N, 5.48.
4.2.6. N-(5-(Phenoxymethyl)-1,3-oxathiolan-2-ylidene)benzenamine (3f)
Pale yellow powder, yield: 0.51 g (90%). IR (KBr) (νmax/cm−1): 1646, 1591, 1354, 1168,
1098 cm−1. 1H NMR (500 MHz, CDCl3): δ = 3.50–3.59 (m, 2 H, CH2), 4.24–4.35 (m, 2 H, CH2),
5.01–5.05 (m, 1 H, CH), 6.96–7.38 (m, 10 H, 10 CH). 13C NMR (125.7 MHz, CDCl3): δ = 33.5
(CH2), 66.9 (CH2), 78.9 (CH), 114.6 (2 CH), 121.2 (2 CH), 121.7 (CH), 124.4 (CH), 129.1 (2 CH),
129.6 (3 CH), 148.9 (C), 158.0 (C), 162.9 (C). EI-MS: 422 (M+, 10), 350 (20), 348 (20), 167
(25), 149 (60), 84 (100), 57 (62). Anal. Calcd (%) for C16H15NO2S (285.36): C, 67.35, H, 5.30,
N, 4.91. Found: C, 67.23, H, 5.21, N, 4.85.
4.2.7. 4-Methyl-N-(5-(phenoxymethyl)-1,3-oxathiolan-2-ylidene)benzenamine (3g)
Pale yellow powder, yield: 0.55 g (92%). IR (KBr) (νmax/cm−1 1646, 1591, 1362, 1172,
1122 cm−1. 1H NMR (500 MHz, CDCl3): δ = 2.36 (s, 3 H, Me), 3.49-3.58 (m, 2 H, CH2), 4.25–
4.28 (m, 1 H, CH), 4.32–4.34 (m, 1 H, CH), 4.99–5.04 (m, 1 H, CH), 6.91 (d, 2 H, 3J = 8.2 Hz,
2 CH), 6.96 (d, 2 H, 3J = 8.3 Hz, 2 CH), 7.02 (t, 1 H, 3J = 7.3 Hz, CH), 7.16 (d, 2 H, 3J = 8.2,
3
2 CH), 7.33 (t, 2 H, J = 7.9 Hz, 2 CH). 13C NMR (125.7 MHz, CDCl3): δ = 20.9 (Me), 33.5
(CH2), 66.9 (CH2), 78.9 (CH), 114.7 (2 CH), 121.0 (2 CH), 121.7 (CH), 129.6 (2 CH), 129.7
(2 CH), 133.9 (C), 146.4 (C), 158.1 (C), 162.6 (C). EI-MS: 450 (M+, 5), 377 (24), 375 (24), 370
(68), 231 (45), 229 (45), 84 (100), 73 (60). Anal. Calcd (%) for C17H17NO2S 299.39): C, 68.20,
H, 5.72, N, 4.68. Found: C, 68.25, H, 5.83, N, 4.75.
4.2.8. 4-Methoxy-N-(5-(phenoxymethyl)-1,3-oxathiolan-2-ylidene)benzenamine (3h)
Pale yellow powder, yield: 0.55 g (88%). IR (KBr) (νmax/cm−1): 1643, 1591, 1352, 1170, 1144,
1101 cm−1. 1H NMR (500 MHz, CDCl3): δ = 3.47–3.56 (m, 2 H, CH2), 3.81 (s, 3 H, MeO), 4.22–
4.26 (m, 1 H, CH), 4.29–4.32 (m, 1 H, CH), 4.98–5.01 (m, 1 H, CH), 6.87 (d, 2 H, 3J = 8.2 Hz,
2 CH), 6.94 (d, 4 H, 3J = 8.7 Hz, 4 CH), 7.02 (t, 1 H, 3J = 7.2 Hz, CH), 7.32 (d, 2 H, 3J = 8.2,
2 CH). 13C NMR (125.7 MHz, CDCl3): δ = 33.5 (CH2), 55.4 (MeO), 66.9 (CH2), 78.8 (CH),
114.4 (2 CH), 114.6 (2 CH), 121.6 (CH), 122.2 (2 CH), 129.6 (2 CH), 142.2 (C), 156.6 (C), 158.0
(C), 162.6 (C). EI-MS: 343 (M+, 10), 270 (85), 306 (66), 292(64), 284 (60), 275 (85), 84 (100),
59 (67). Anal. Calcd (%) for C17H17NO3S (315.36): C, 64.74, H, 5.43, N, 4.44. Found: C, 64.65,
H, 5.38, N, 4.35.
4.2.9. N-(5-Isopropoxymethyl-1,3-oxathiolan-2-ylidene)benzenamine (3i)
Pale yellow powder, yield: 0.45 g (89%). IR (KBr) (νmax/cm−1): 1649, 1581, 1340, 1155,
1144 cm−1. 1H NMR (500 MHz, CDCl3): δ = 1.22 (d, 6 H, 3J = 6.2, 2 Me), 3.34-3.42 (m, 2 H,