Method for preparing 2-phenyl-5-phenyl-5-methylthiocyano-4, 5-dihydrothiazole compound through silver catalysis
A technology for the catalytic preparation of methylthiocyanate, which is applied in the direction of organic chemistry, can solve the problems of low reaction efficiency, many reaction steps, and limited application range, and achieve the effect of simple and easy-to-obtain raw materials, high added value, and wide application
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Embodiment 1
[0040] Embodiment 1: the preparation of 4a product
[0041]
[0042] At room temperature, add 364mg (3mmol) of N-methylbenzylamine 1a, 373mg (3mmol) of thiophenol 2a and 527mg (4.5mmol) of thiocyanoacetic acid 3a in a 25mL round bottom flask, and then sequentially add With 10 mL of acetonitrile, 165 mg (0.6 mmol) of silver carbonate and 636 mg (6 mmol) of sodium carbonate, the reaction was stirred at 90° C. for 10 hours. After cooling, add 10mL saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 10mL each time, combine the organic phases, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain by 200-300 mesh silica gel column chromatography Pure 4a (828 mg, 89% yield, yellow oily liquid). 4a 1 H-NMR spectrum see figure 1, 4a 13 C-NMR spectrum see figure 2 .
[0043] 1 H NMR (400MHz, CDCl 3 ):δ7.81-7.74(m,2H),7.68(br s,1H),7.49-7.44(m,1H),7.42-7.26(m,7H),6.70(d,J=15.7Hz,1H) ,6.37(dt,J=15.7,6.4Hz,1H),4.63(t,J=6...
Embodiment 2
[0046] Embodiment 2: Preparation of 4b product
[0047]
[0048] At room temperature, add 406mg (3mmol) of 4-methyl-N-methylbenzylamine 1b, 373mg (3mmol) of thiophenol 2a and 527mg (4.5mmol) of thiocyanoacetic acid in a 25mL round bottom flask 3a, then 10 mL of acetonitrile, 165 mg (0.6 mmol) of silver carbonate and 636 mg (6 mmol) of sodium carbonate were sequentially added, and the reaction was stirred at 90° C. for 10 hours. After cooling, add 10 mL saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, distill off the solvent, and obtain by 200-300 mesh silica gel column chromatography Pure product 4b (878 mg, yield 90%, yellow oily liquid). 4b 1 H-NMR spectrum see image 3 , 4b 13 C-NMR spectrum see Figure 4 .
[0049] 1 H NMR (400MHz, CDCl 3 ):δ7.67(d, J=8.3Hz, 2H), 7.29-7.13(m, 5H), 6.73(d, J=8.2Hz, 2H), 6.52(d, J=15.7Hz, 1H), 6.26 -6.17(m,...
Embodiment 3
[0052] Embodiment 3: Preparation of 4c product
[0053]
[0054] At room temperature, 454mg (3mmol) of 4-methoxy-N-methylbenzylamine 1c, 373mg (3mmol) of thiophenol 2a and 527mg (4.5mmol) of thiocyanate were added to a 25mL round bottom flask. Acetic acid 3a was added successively to 10 mL of acetonitrile, 165 mg (0.6 mmol) of silver carbonate and 636 mg (6 mmol) of sodium carbonate, and the reaction was stirred at 90° C. for 10 hours. After cooling, add 10 mL saturated aqueous sodium chloride solution to the system, extract 3 times with ethyl acetate, 10 mL each time, combine the organic phases, dry with anhydrous sodium sulfate, distill off the solvent, and obtain by 200-300 mesh silica gel column chromatography Pure product 4c (939 mg, yield 92%, yellow oily liquid). 4c 1 H-NMR spectrum see Figure 5 , 4c 13 C-NMR spectrum see Image 6 .
[0055] 1 H NMR (400MHz, CDCl 3 ):δ8.03(br s,1H)7.68(d,J=7.4Hz,2H),7.45(d,J=7.0Hz,2H),7.29-7.13(m,5H),6.55(d,J= 15.8Hz,1H),6....
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