Page 170 - 《精细化工》2022年第12期

·2536· 精细化工 FINE CHEMICALS 第 39 卷

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(s, 3H, 6-CH 3), 2.48 (s, 3H, 5-CH 3); CNMR 〔100 2.59 (s, 3H, 6-CH 3), 2.49 (s, 3H, 5-CH 3); CNMR 〔100
MHz, (CD 3) 2CO〕, δ: 163.9, 157.8, 150.3, 139.3, 132.4, MHz, (CD 3) 2CO〕, δ: 164.0, 157.5, 149.9, 138.3, 132.5,
128.3, 127.9, 126.9, 124.6, 121.7, 116.2, 44.3, 13.3, 12.5; 132.2, 129.7, 128.2, 124.6, 121.6, 117.8, 43.7, 13.3, 12.6;
1
1
IR (KBr), v/cm : 3438 (N—H), 1579 (C==N), 1334, IR (KBr), v/cm : 3470 (N—H), 1591 (C==N), 1332,
+
+
1193 (CF 3); EI-MS (M ), m/Z，实测值（计算值）：337.26 1185 (CF 3); EI-MS (M ), m/Z，实测值（计算值）：371.18
(337.09); 元素分析，C 16H 14F 3N 3S，实验值（计算值）： (371.05); 元素分析，C 16H 13ClF 3N 3S, 实验值（计算
w(C) = 57.14% (56.96%), w(H) = 4.12% (4.18%), w(N) = 值）：w(C) = 51.56% (51.69%), w(H) = 3.47% (3.52%),
12.36% (12.46%)。 w(N) = 11.09% (11.30%)。
5,6-二甲基-2-三氟甲基-4-(4-氟苄氨基)噻吩并 5,6-二甲基-2-三氟甲基-4-(3-氯苄氨基)噻吩并
[2,3-d]嘧啶（Ⅲb）：白色固体，收率 83%, m.p. 131~ [2,3-d]嘧啶（Ⅲf）：白色固体，收率 79%, m.p. 116~
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132 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.55 (s, 1H, 117 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.54 (s, 1H,
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NH), 7.51~7.05 (m, 4H, Ar—H), 4.85 (s, 2H, Ar—CH 2), NH), 7.45~7.25 (m, 4H, Ar—H), 4.87 (s, 2H, Ar—CH 2),
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2.58 (s, 3H, 6-CH 3), 2.49 (s, 3H, 5-CH 3); CNMR 〔100 2.59 (s, 3H, 6-CH 3), 2.49(s, 3H, 5-CH 3); CNMR 〔100
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MHz, (CD 3) 2CO〕, δ: 163.9, 163.1, 160.7, 157.50, 149.9, MHz, (CD 3) 2CO〕, δ: 164.0, 157.5, 149.9, 141.8, 133.6,
135.4, 132.4, 130.0, 121.6, 117.8, 114.9, 114.7, 43.7, 132.5, 129.9, 128.1, 126.9, 126.5, 124.6, 121.6, 117.8,
1
13.3, 12.52; IR (KBr), v/cm : 3514 (N—H), 1579 43.9, 13.3, 12.5; IR (KBr), v/cm : 3455 (N—H), 1586
1
+
(C==N), 1334, 1166 (CF 3); EI-MS (M ), m/Z，实测值（计 (C==N), 1332, 1187 (CF 3); EI-MS (M ), m/Z，实测值（计
+
算值）：355.25 (355.08); 元素分析，C 16H 13F 4N 3S, 实 算值）：371.19 (371.05); 元素分析 C 16H 13ClF 3N 3S, 实
验值（计算值）：w(C) = 53.80% (54.08%), w(H) = 3.54% 验值（计算值）：w(C) = 51.51% (51.69%), w(H) = 3.48%
(3.69%), w(N) = 11.75% (11.83%)。 (3.52%), w(N) = 11.41% (11.30%)。
5,6-二甲基-2-三氟甲基-4-(3-氟苄氨基)噻吩并 5,6-二甲基-2-三氟甲基-4-(2-氯苄氨基)噻吩并
[2,3-d]嘧啶（Ⅲc）：白色固体，收率 79%, m.p. 111~ [2,3-d]嘧啶（Ⅲg）：白色固体，收率 89%, m.p. 154~
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112 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.45 (s, 1H, 156 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.57 (s, 1H,
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NH), 7.34~6.98 (m, 4H, Ar—H), 4.89 (s, 2H, Ar—CH 2), NH), 7.44~7.27 (m, 4H, Ar—H), 4.96 (s, 2H, Ar—CH 2),
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2.60 (s, 3H, 6-CH 3), 2.49(s, 3H, 5-CH 3); CNMR 〔100 2.64 (s, 3H, 6-CH 3), 2.59 (s, 3H, 5-CH 3); CNMR 〔100
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MHz, (CD 3) 2CO〕, δ: 164.7, 162.3, 158.2, 150.6, 143.0, MHz, (CD 3) 2CO〕, δ: 164.0, 157.5, 150.3, 136.1, 132.9,
133.2, 130.7, 125.3, 124.4, 122.3, 118.5, 115.4, 114.3, 132.7, 129.9, 129.2, 128.8, 126.9, 124.5, 121.7, 117.9,
1
44.6, 14.0, 13.2; IR (KBr), v/cm : 3493 (N—H), 1589 42.2, 13.3, 12.6; IR (KBr), v/cm : 3526 (N—H), 1579
1
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(C==N), 1330, 1200 (CF 3); EI-MS (M ), m/Z，实测值（计 (C==N), 1330, 1136 (CF 3); EI-MS (M ), m/Z，实测值（计
+
算值）：355.15 (355.08); 元素分析，C 16H 13F 4N 3S，实 算值）：371.24 (371.05); 元素分析，C 16H 13ClF 3N 3S，
验值（计算值）：w(C) = 53.84% (54.08%), w(H) = 3.58% 实验值（计算值）：w(C) = 51.58% (51.69%), w(H) =
(3.69%), w(N) = 11.79% (11.83%)。 3.46% (3.52%), w(N) = 11.28% (11.30%)。
5,6-二甲基-2-三氟甲基-4-(2-氟苄氨基)噻吩并 5,6-二甲基-2-三氟甲基-4-(4-溴苄氨基)噻吩并
[2,3-d]嘧啶（Ⅲd）：白色固体，收率 81%, m.p. 148~ [2,3-d]嘧啶（Ⅲh）：白色固体，收率 81%, m.p. 163~
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149 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.56 (s, 1H, 164 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.50 (s, 1H,
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NH), 7.31~7.09 (m, 4H, Ar—H), 4.93 (s, 2H, Ar—CH 2), NH), 7.48~7.43 (m, 4H, Ar—H), 4.84 (s, 2H, Ar—CH 2),
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2.61 (s, 3H, 6-CH 3), 2.49 (s, 3H, 5-CH 3); CNMR 〔100 2.59 (s, 3H, 6-CH 3), 2.49 (s, 3H, 5-CH 3); CNMR 〔100
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MHz, (CD 3) 2CO〕, δ: 164.0, 162.2, 159.8, 157.6, 149.9, MHz, (CD 3) 2CO〕, δ: 164.0, 157.4, 149.9, 138.8, 132.5,
132.6, 130.1, 128.9, 126.0, 124.5, 124.1, 121.6, 117.9, 131.2, 130.1, 124.6, 121.6, 120.3, 117.8, 43.7, 13.3, 12.5;
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1
115.1, 33.3, 13.2, 12.5; IR (KBr), v/cm : 3457 (N—H), IR (KBr), v/cm : 3481 (N—H), 1583 (C==N), 1334,
+
+
1583 (C==N), 1334, 1164 (CF 3); EI-MS (M ), m/Z，实测 1168 (CF 3); EI-MS (M ), m/Z，实测值（计算值）：415.19
值（计算值）：355.21 (355.08)；元素分析，C 16H 13F 4N 3S, (415.00); 元素分析，C 16H 13BrF 3N 3S, 实验值（计算
实验值（计算值）：w(C) = 53.78% (54.08%), w(H) = 值）：w(C) = 46.29% (46.17%), w(H) = 3.25% (3.15%),
3.75% (3.69%), w(N) = 11.87% (11.83%)。 w(N) = 10.24% (10.09%)。
5,6-二甲基-2-三氟甲基-4-(4-氯苄氨基)噻吩并 5,6-二甲基-2-三氟甲基-4-(3-溴苄氨基)噻吩并
[2,3-d]嘧啶（Ⅲe）：白色固体，收率 84%, m.p. 166~ [2,3-d]嘧啶（Ⅲi）：白色固体，收率 79%, m.p. 95~96 ℃;
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168 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.51 (s, 1H, 1 HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.69 (s, 1H, NH),
NH), 7.49~7.33 (m, 4H, Ar—H), 4.86 (s, 2H, Ar—CH 2), 7.50~7.28 (m, 4H, Ar—H), 4.87 (s, 2H, Ar—CH 2), 2.60