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·356· 精细化工 FINE CHEMICALS 第 36 卷
1-[2-(2-氯苯基)-4-(4-甲氧基苯基)噻唑-5-基]- m/Z: 实测值(计算值): 483.07 (483.46)。
3-(3,5-二氟苯甲酰基)脲(Ⅵa): 黄色固体, 产率 91.5%, 1-[2-(3-氟苯基)-4-(4-甲氧基苯基)噻唑-5-基]-
1
m.p. 230~232 ℃。HNMR (DMSO-d 6 , 500 MHz), δ: 3.84 3-(3,5-二氟苯甲酰基)脲(Ⅵe): 黄色固体, 产率 82.3%,
1
(s, 3H), 7.11 (d, J=8.6 Hz, 2H), 7.46~7.48 (m, 2H), m.p.>250 ℃。HNMR (DMSO-d 6, 500 MHz), δ: 3.85 (s,
7.60~7.63 (m, 2H), 7.72 (d, J=6 Hz, 2H), 7.83 (d, 3H), 7.11 (d, J=8.7 Hz, 2H), 7.27~7.31 (m, 1H),
J=8.6 Hz, 2H), 8.23~8.25 (m, 1H), 11.65 (s, 2H)。 7.51~7.56 (m, 1H), 7.60~7.64 (m, 1H), 7.72~7.77 (m,
13 CNMR (DMSO-d 6 , 125 MHz), δ: 167.0, 163.6, 163.5, 6H), 11.69 (d, J=23.4 Hz, 2H)。 CNMR (DMSO-d 6 ,
13
161.6, 159.6, 154.2, 151.0, 139.5, 135.7, 132.0, 131.2, 125 MHz), δ: 167.0,164.0, 162.0, 162.6, 159.6, 157.0,
131.1, 130.7, 130.6, 130.2, 129.5, 128.1, 126.3, 114.9, 151.0, 140.5, 136.0, 135.9, 131.8, 131.7, 129.5, 129.0,
1
112.6, 112.5, 112.3, 109.1, 55.7。IR (KBr), ν/cm : 126.2, 122.2, 116.9, 116.7, 114.9, 112.6, 112.4, 112.3,
1
3226, 3074, 1708, 1564, 1457, 1328, 1251, 1135, 808, 112.2, 109.2, 55.7。IR (KBr), ν/cm : 3227, 3076, 1706,
+
760, 736, 720。EI-MS (M ), m/Z: 实测值(计算值): 1564, 1457, 1335,1249, 1145, 1130, 810, 790, 718。EI-
499.12 (499.96)。 MS (M ), m/Z: 实测值(计算值) : 483.05 (483.46)。
+
1-[2-(3-氯苯基)-4-(4-甲氧基苯基)噻唑-5-基]- 1-[2-(4-氟苯基)-4-(4-甲氧基苯基)噻唑-5-基]-
3-(3,5-二氟苯甲酰基)脲(Ⅵb): 黄色固体, 产率 89.9%, 3-(3,5-二氟苯甲酰基)脲(Ⅵf): 黄色固体, 产率 93.6%,
1
1
m.p. 232~233 ℃。 HNMR (DMSO-d 6 , 500 MHz), δ: m.p.>250 ℃。HNMR (DMSO-d 6, 500 MHz), δ: 3.85 (s,
3.85 (s, 3H), 7.12 (d, J=8.8 Hz, 2H), 7.50~7.51 (m, 3H), 7.11 (d, J=8.0 Hz, 2H), 7.31~7.34 (m, 2H), 7.76 (d,
2H), 7.56~7.58 (m, 2H), 7.72 (d, J=6 Hz, 2H), 7.75~ J=6.6 Hz, 1H), 7.73~7.77 (m, 4H), 8.00(s, 1H), 11.60
13
13
7.79 (m, 3H), 11.66 (s, 1H), 11.70 (s, 1H)。 CNMR (s, 1H), 11.68 (s, 1H)。 CNMR (DMSO-d 6 , 125 MHz),
(DMSO-d 6 , 125 MHz), δ: 163.7, 161.6,159.6, 156.7, δ: 166.9, 162.5, 161.3, 159.5, 157.5, 150.9, 140.7,
150.9, 140.6, 135.7, 134.4, 131.6, 129.8, 129.5, 129.0, 130.3, 129.4, 128.3, 128.2, 128.1, 126.3, 123.8, 122.8,
128.2, 126.2, 125.2, 124.7, 114.9, 114.3, 112.6, 112.3, 116.6, 116.3, 115.4, 115.1, 114.8, 55.7。IR (KBr),
1
111.4, 111.1, 107.2, 55.7。IR (KBr), ν/cm : 3234, ν/cm : 3225, 3072, 1702, 1561, 1448, 1328, 1243,
1
3077, 1706, 1569, 1455, 1337,1247, 1130, 810, 790, 1140, 1129, 832, 805, 723。EI-MS (M ) ，m/Z: 实测
+
+
740, 718。EI-MS (M ), m/Z: 实测值(计算值): 499.14
值(计算值): 483.06 (483.46)。
(499.96)。
1-[2-(2-甲基苯基)-4-(4-甲氧基苯基)噻唑-5-基]-
1-[2-(4-氯苯基)-4-(4-甲氧基苯基)噻唑-5-基]- 3-(3,5-二氟苯 甲酰 基)脲(Ⅵg): 黄色固体, 产率
3-(3,5-二氟苯甲酰基)脲(Ⅵc): 黄色固体, 产率 87.0%, 87.3%, m.p. 228.7~229 ℃。HNMR (DMSO-d 6 , 500 MHz),
1
1
m.p. >250 ℃。HNMR (DMSO-d 6, 500 MHz), δ: 3.81 (s, δ: 2.61 (s, 3H), 3.84 (s, 3H), 7.11 (d, J=8.6 Hz, 2H),
3H), 7.12 (d, J=8.3 Hz, 2H), 7.53 (d, J=8.5 Hz, 2H), 7.32~7.34(m, 1H), 7.36~7.37 (m, 2H), 7.59~7.62 (m,
7.76 (d, J=8.8Hz, 2H), 7.86 (d, J=6.0 Hz, 1H), 7.89 (d, 1H), 7.73~7.77 (m, 5H), 11.58 (s, 1H), 11.64 (s, 1H)。
J=8.1 Hz, 1H), 7.94 (d, J=8.7 Hz, 2H), 8.04 (s, 1H), 13 CNMR (DMSO-d 6 , 125 MHz), δ: 161.3, 159.5, 159.0,
13
11.66(d, J=37.1 Hz, 2H)。 CNMR (DMSO-d 6 , 125 151.0, 140.1, 136.2, 135.8, 132.8, 132.2, 129.6, 129.5,
MHz), δ: 166.9, 163.3, 161.1, 159.5, 157.2, 150.9, 129.4, 128.5, 126.9, 126.6, 114.9, 112.6, 112.4, 55.7,
140.6, 134.6, 132.7, 129.6,128.6, 127.7, 126.2, 123.9, 21.9。IR (KBr), ν/cm : 3234, 3080, 1712, 1570, 1467,
1
123.5, 122.8, 122.7, 115.3, 115.4, 114.9, 55.7。IR (KBr), 1331, 1259, 1137, 810, 766, 716。EI-MS (M ), m/Z:
+
1
ν/cm : 3223, 3070, 1702, 1569, 1453, 1324, 1241, 实测值(计算值): 479.21 (479.50)。
+
1129, 832, 805, 733, 725。EI-MS (M ), m/Z: 实测值
1-[2-(3-甲基苯基)-4-(4-甲氧基苯基)噻唑-5-基]-
(计算值): 499.11 (499.96)。
3-(3,5-二氟苯甲酰基)脲(Ⅵh): 黄色固体, 产率 81.4%,
1-[2-(2-氟苯基)-4-(4-甲氧基苯基)噻唑-5-基]-
1
m.p. 221~223 ℃。HNMR (DMSO-d 6 , 500 MHz), δ: 2.37
3-(3,5-二氟苯甲酰基)脲(Ⅵd): 黄色固体, 产率 95.8%, (s, 3H), 3.83 (s, 3H), 7.09 (d, J=8.7 Hz, 2H), 7.24 (d,
1
m.p. 220~221 ℃。 HNMR (DMSO-d 6 , 500 MHz), δ: J=7.6 Hz, 1H), 7.33~7.36 (m, 1H), 7.57~7.60 (m, 1H),
3.86 (s, 3H), 7.13 (d, J=8.8 Hz, 2H), 7.35~7.38 (m, 1H), 7.64 (d, J=7.2 Hz, 1H), 7.70~7.74 (m, 5H), 11.60 (s,
13
7.41~7.44 (m, 1H), 7.66 (d, J=8.2 Hz, 2H), 7.73 (d, 1H), 11.67 (s, 1H)。 CNMR (DMSO-d 6 , 125 MHz), δ:
J=5.8 Hz 2H), 7.77 (d, J=8.7 Hz, 2H), 8.25~8.28 (m, 166.9, 163.5, 161.5, 161.4, 159.5, 158.7, 150.9, 140.3,
13
1H), 11.68 (d, J=22.7 Hz, 2H)。 CNMR (DMSO-d 6 , 138.8, 135.5, 133.6, 130.7, 129.3, 128.0, 126.6, 126.5,
125 MHz), δ: 164.8, 163.8, 163.7, 161.8, 161.7, 159.6, 123.3, 114.9, 112.4, 112.2, 112.1, 111.9, 109.2, 55.7,
1
158.4，151.0, 148.9, 139.5, 129.8, 129.5, 128.3, 126.3, 21.4。IR (KBr), ν/cm : 3237, 3079, 1708, 1569, 1459,
+
125.6, 116.9, 116.7, 114.9, 112.6, 112.3, 112.1, 111.9, 1337, 1251, 1131, 810, 789, 721。EI-MS (M ), m/Z:
1
109.2, 55.7。IR (KBr), ν/cm : 3221, 3071, 1700, 1558, 实测值(计算值): 479.24 (479.50)。
+
1455, 1321, 1245, 1142, 1134, 808, 760, 720。EI-MS (M ), 1-[2-(4-甲基苯基)-4-(4-甲氧基苯基)噻唑-5-基]-
