Method for preparing isonitrile compound
A compound and isonitrile technology, which is applied in the field of preparation of isonitrile compounds, can solve the problems of poor compatibility of substrate functional groups, narrow types of isonitriles, and low efficiency, and achieve stable performance, low cost, and less pollution.
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Embodiment 1
[0032] Embodiment 1: A method for synthesizing isonitrile compounds with primary amines, adopts the following process steps:
[0033] Sodium difluorochloroacetate 1 (0.2mmol, 31mg), K 2 CO 3 (0.2mmol, 28mg) and p-methoxyaniline (2a, 0.1mmol, 12.3mg) were placed in a 25mL reaction tube, vacuumed and filled with nitrogen (three times). DMF (1 mL) was injected with a syringe under nitrogen protection. Stir in an oil bath at 100°C for 12 hours, cool to room temperature, filter, add the reaction solution and 20 mL of water to the extraction funnel, then add 25 mL of dichloromethane for extraction, then take the organic layer and add a small amount of silica gel to spin dry column chromatography to obtain Product 3a as yellow solid (70% yield).
[0034] The reaction process of above-mentioned steps is shown in following formula (1):
[0035]
[0036] The NMR data of product 3a are as follows:
[0037] 1 H NMR (400MHz, CDCl 3 )δ7.32(d,J=8.9Hz,2H),6.92–6.84(d,2H),3.83(s,3H)....
Embodiment 2
[0038] Embodiment 2: A method for synthesizing isonitriles with primary amines, using the following process steps:
[0039] Sodium difluorochloroacetate 1 (0.2mmol, 31mg), K 2 CO 3(0.2mmol, 28mg) and N,N-dimethyl-p-phenylenediamine (2b, 0.1mmol, 13.6mg) were placed in a 25mL reaction tube, vacuumed and filled with nitrogen (three times). DMF (1 mL) was injected with a syringe under nitrogen protection. Stir in an oil bath at 100°C for 12 hours, cool to room temperature, filter, add the reaction solution and 20 mL of water to the extraction funnel, then add 25 mL of dichloromethane for extraction, then take the organic layer and add a small amount of silica gel to spin dry column chromatography to obtain White solid product 3b (72% yield).
[0040] The reaction process of above-mentioned steps is shown in following formula (2):
[0041]
[0042] The NMR data of product 3b are as follows:
[0043] 1 H NMR (400MHz, CDCl 3 )δ7.22(d, J=8.9Hz, 2H), 6.59(d, J=9.1Hz, 2H), 2....
Embodiment 3
[0044] Embodiment 3: A method for synthesizing isonitrile compounds with primary amines, adopts the following process steps:
[0045] Sodium difluorochloroacetate 1 (0.2mmol, 31mg), K 2 CO 3 (0.2mmol, 28mg) and p-phenylenediamine (2c, 0.1mmol, 11mg) were placed in a 25mL reaction tube, vacuumed and filled with nitrogen (three times). DMF (1 mL) was injected with a syringe under nitrogen protection. Stir in an oil bath at 100°C for 12 hours, cool to room temperature, filter, add the reaction solution and 20 mL of water to the extraction funnel, then add 25 mL of dichloromethane for extraction, then take the organic layer and add a small amount of silica gel to spin dry column chromatography to obtain White solid product 3c (83% yield)
[0046] The reaction process of above-mentioned steps is shown in following formula (3):
[0047]
[0048] The NMR data of product 3c are as follows:
[0049] 1 H NMR (400MHz, CDCl 3 )δ7.14(d, J=8.4Hz, 2H), 6.58(d, J=8.7Hz, 2H), 3.94(s,...
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