N-phenyl-dichloroacetamide and derivatives as well as preparation method and application thereof
A technology of phenyl dichloroacetamide and dichloroacetamide, which is applied in the field of preparation of antitumor drugs, can solve the problems of high dosage and insufficient anticancer activity
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Embodiment 1
[0071] The synthesis of embodiment 1N-phenyl dichloroacetamide
[0072] Add 20ml of dry toluene and 0.487g (5.2mmol) of aniline to a 50ml two-necked round bottom flask. Add 5ml of dry toluene and 0.992g (6.8mmol, 1.3eqv) of dichloroacetyl chloride into a constant pressure dropping funnel, slowly drop them into a two-necked round bottom flask at room temperature, heat up to reflux, and the reaction temperature is 110-115°C. 2 hours. TLC detected that the reaction was complete, and the solvent toluene, hydrogen chloride and unreacted dichloroacetyl chloride were removed by rotary evaporation under reduced pressure to obtain 1.062 g of white powder. Yield 99%.
[0073] Table 1 provides some compounds and their raw materials synthesized by the method of Example 1, and the yields are above 96%.
[0074] Table 1 adopts the part compound synthesized by the method of embodiment 1
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example 2
[0084] Example 2 Synthesis of N-(2-chloro-4-ethoxycarbonyl-phenyl) dichloroacetamide (compound 43)
[0085] The synthetic reaction formula is as follows:
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[0087] Compound 43
[0088] The operation steps are as follows:
[0089] Add 9ml of dry ethanol to a 25ml round bottom flask, cool to -10°C in an ice-salt bath, and slowly add 2.4ml of SOCl dropwise 2 , control the temperature below zero during the dropwise addition, then add 0.516g of 3-chloro-4-amino-benzoic acid (3mmol), remove the ice-salt bath after half an hour, after the temperature rises to room temperature, heat to 50°C, and react for 20 After 1 hour, ethanol and hydrogen chloride gas were evaporated under reduced pressure to obtain 0.675 g of 2-chloro-4-ethoxycarbonyl-aniline hydrochloride, with a yield of 95%.
[0090] Using the 2-chloro-4-ethoxycarbonyl-aniline hydrochloride obtained by the above method, the target product compound 43, 2-chloro-4-ethoxycarbonyl-aniline salt of this example was syn...
example 3
[0092] Example 3 Synthesis of N-(2-chloro-4-isopropoxycarbonyl-phenyl) dichloroacetamide (compound 44)
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[0094] Compound 44
[0095] Add 60ml of dry isopropanol to a 100ml round bottom flask, cool to -10°C in an ice-salt bath, and slowly add 12ml of SOCl dropwise 2 , control the temperature below zero during the dropwise addition, then add 5.16g of 3-chloro-4-amino-benzoic acid (30mmol), remove the ice-salt bath after half an hour, after the temperature rises to room temperature, heat to 82°C for reflux, and react After 36 hours, isopropanol and hydrogen chloride gas were evaporated under reduced pressure to obtain 7.210 g of 2-chloro-4-isopropoxycarbonyl-aniline hydrochloride with a yield of 96%.
[0096]Using the 2-chloro-4-isopropoxycarbonyl-aniline hydrochloride obtained by the above method, the target product compound 44, 2-chloro-4-isopropoxycarbonyl- The addition amounts of aniline hydrochloride and dichloroacetyl chloride were 0.531g and 0.407g respective...
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