A kind of method for preparing oxamide ester
A technology for oxamide ester and diazonium ester, which is applied in the field of preparing oxamide ester, can solve the problems of harsh reaction conditions, narrow substrate range, limited application of reagents, etc., and achieves the effects of mild reaction conditions and improved universality
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Embodiment 1
[0030]
[0031] Add 1a (0.2 mmol, 50.5 mg), 2 (0.8 mmol, 116.0 mg), acetonitrile MeCN (1.0 mL), TBHP (0.6 mmol, 84 μL) in one portion to the test tube. Then the system was heated and stirred at 40° C. in air for 12 hours, the reaction system was quenched with saturated sodium sulfite solution, extracted three times with ethyl acetate, and the organic layers were combined and dried over anhydrous sodium sulfate. Then the solvent was removed, silica gel was adsorbed, and the product oxalamide ester 3a was obtained by column chromatography with a yield of 77%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis. The oxidant used in the reaction is replaced by tert-butyl peroxybenzoate (TBPB), and the rest remain unchanged, and the target product cannot be obtained; or, the reaction solvent is replaced by N,N -Dimethylformamide (DMF), the rest remain unchange...
Embodiment 2
[0034]
[0035] Add 1b (0.2 mmol, 35.3 mg), 2 (0.8 mmol, 116.0 mg), acetonitrile MeCN (1.0 mL), TBHP (0.6 mmol, 84 μL) in one portion to the test tube. Then the system was heated and stirred at 40° C. in air for 12 hours, the reaction system was quenched with saturated sodium sulfite solution, extracted three times with ethyl acetate, and the organic layers were combined and dried over anhydrous sodium sulfate. Then the solvent was removed, silica gel was adsorbed, and the product oxalamide ester 3b was obtained by column chromatography with a yield of 70%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis. Replace reaction substrate 1b with , the product cannot be obtained under the remaining unchanged reaction conditions.
[0036] 1 H NMR (400 MHz, DMSO) δ 8.28 (s, 1H), 7.99 (s, 1H), 7.54-7.27 (m,5H), 5.23 (s, 2H). 13 C NMR (100 MHz, DMSO) δ 160.9...
Embodiment 3
[0038]
[0039] 1c (0.2 mmol, 41.3 mg), 2 (0.8 mmol, 116.0 mg), acetonitrile MeCN (1.0 mL) and TBHP (0.6 mmol, 84 μL) were added to the test tube at one time. Then the system was heated and stirred at 40° C. in air for 12 hours, the reaction system was quenched with saturated sodium sulfite solution, extracted three times with ethyl acetate, and the organic layers were combined and dried over anhydrous sodium sulfate. Then the solvent was removed, silica gel was adsorbed, and the product oxalamide ester 3c was obtained by column chromatography with a yield of 68%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.
[0040] 1 H NMR (400 MHz, DMSO) δ 8.22 (s, 1H), 7.96 (s, 1H), 7.37 (dd, J =4.6, 1.7 Hz, 1H), 7.02 – 6.88 (m, 2H), 4.37 (t, J = 6.6 Hz, 2H), 3.20 (t, J =6.6 Hz, 2H). 13 C NMR (100 MHz, DMSO) δ 160.9, 158.7, 139.4, 127.1, 126.0, 124.6, 6...
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