Schiff base containing carbazyl and thiadiazolyl and preparation method thereof
A thiadiazolyl and carbazole-based technology, which is applied in the field of chemical synthesis, can solve problems such as low yield, large amount of solvent used, and long reaction time, and achieve shortened reaction time, short reaction time, and fast reaction speed Effect
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Embodiment 1
[0036] 1) Add 0.005mol 3,6-diethylacyl-9-ethylcarbazole, 0.011mol 2-amino-1,3,4-thiadiazole and 0.011mol p-toluenesulfonic acid to a dry mortar, That is, 3,6-diethylacyl-9-ethylcarbazole: 2-amino-1,3,4-thiadiazole: p-toluenesulfonic acid is 1:2.2:2.2; Grinding at room temperature for 15min, at this time TLC Monitoring showed that the raw material points of 3,6-diacetyl-9-ethylcarbazole and 2-amino-1,3,4-thiadiazole disappeared, indicating that the raw materials were completely reacted, and then stood to remove water for 30 minutes to obtain a mixture; Wherein the developer is a mixed solvent of ethyl acetate and sherwood oil with a volume ratio of 1:3;
[0037] 2) After the mixture was washed with water and suction filtered, 3,6-diacetyl-9-ethylcarbazole 2-amino-1,3,4-thiadiazole Schiff base was obtained. m.p.: 169.3-171.5°C, yield 84.8%.
[0038] IR (KBr tablet): 3045 (Ar-H); 2975 (saturated C-H); 1657 (C=N); 1611, 1580, 1487 (benzene ring skeleton vibration); 1386 (-CH 3 ...
Embodiment 2
[0042] 1) Add 0.005mol 3-acetyl-9-methylcarbazole, 0.006mol 2-amino-5-p-chlorophenyl-1,3,4-thiadiazole and 0.006mol p-toluene to a dry mortar Sulphonic acid was ground at room temperature for 16min. At this time, TLC monitoring showed that the raw material sites of 3-acetyl-9-methylcarbazole and 2-amino-5-p-chlorophenyl-1,3,4-thiadiazole disappeared, Indicates that the raw materials are completely reacted, and then left to stand for 30 minutes to obtain a mixture; wherein the developer is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3;
[0043] 2) After the mixture was washed with water and suction filtered, 3-acetyl-9-methylcarbazole 2-amino-5-p-chlorophenyl-1,3,4-thiadiazole Schiff base was obtained. m.p.: 184.6-188.5°C, yield 82.3%.
[0044] IR (KBr tablet): 3053 (Ar-H); 2929, 2820 (saturated C-H), 1595 (C=N), 1479 (benzene ring skeleton vibration); 1355 (-CH 3 ); 1246(C-N); 627(C-S)
[0045] 1 H NMR (CDCl 3 -d 6 ,400Hz,TMS internal st...
Embodiment 3
[0048] 1) Add 0.005mol 3-acetyl-9-ethylcarbazole, 0.006mol 2-amino-5-methyl-1,3,4-thiadiazole and 0.006mol p-toluenesulfonic acid to a dry mortar , Grinding at room temperature for 15 minutes, TLC monitoring at this time showed that the raw material sites of 3-acetyl-9-ethylcarbazole and 2-amino-5-methyl-1,3,4-thiadiazole disappeared, indicating that the raw materials were completely reacted , and then left to stand for 30min to obtain a mixture; wherein the developing agent is a mixed solvent of ethyl acetate and sherwood oil with a volume ratio of 1:3;
[0049] 2) After the mixture was washed with water and suction filtered, 3-acetyl-9-ethylcarbazole 2-amino-5-methyl-1,3,4-thiadiazole Schiff base was obtained. m.p.>300°C, yield 86.7%.
[0050] IR (KBr tablet): 3053 (Ar-H); 2983 (saturated C-H); 1642 (C=N); 1564 (benzene ring skeleton vibration); 1487 (-CH2-); 1378 (-CH 3 ); 1223(C-N); 627(C-S)
[0051] 1 H NMR (CDCl 3 -d 6 ,400Hz, TMS internal standard, δ:ppm):7.82(m,4...
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