Improved method for preparing benzo[d][1,2,3] thiadiazole-7-formic acid trifluoroacetate
A technology of benzothiadiazole and thiadiazole, which is applied in the direction of organic chemistry and can solve the problem of low yield
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[0017] The preparation method of benzo[d][1,2,3]thiadiazole-7-formic acid trifluoroethyl ester of the present invention comprises the steps:
[0018] (1) Synthesis of methyl m-aminobenzoate:
[0019] Mix m-aminobenzoic acid and methanol, add thionyl chloride dropwise under temperature control, and then heat to reflux until the raw materials are completely converted. The material ratio of m-aminobenzoic acid and thionyl chloride is 1:1.5-4 (equivalent ratio), and the reaction time is 4 hours to 10 hours.
[0020] (2) Synthesis of N-(3-methoxycarbonylphenyl)-thiourea:
[0021] Dissolve methyl m-aminobenzoate in chlorobenzene, add thiocyanate and surfactant in batches, and react at 50°C to 120°C for 8 hours to 15 hours to obtain N-(3-methoxycarbonylphenyl) - Thiourea;
[0022] Wherein: said thiocyanate is potassium thiocyanate, sodium thiocyanate or ammonium thiocyanate, and said surface active agent of the table can be quaternary ammonium salt (such as triethylbenzyl ammonium...
Embodiment
[0035] (1) Synthesis of methyl m-aminobenzoate:
[0036]
[0037] Add 200 mL of anhydrous methanol into a 500 mL three-neck flask, stir with a magnetic force, cool to -5°C in an ice-salt bath, and add m-aminobenzoic acid (34.3 g, 0.25 mol) while stirring. Measure SOCl 2 (65.3mL, 0.9mol) was placed in a constant-pressure dropping funnel and added dropwise, controlling the temperature below 0°C. After the dropwise addition, stir for 15 minutes, remove the ice bath, replace the heating reflux device, and reflux for 5 hours. Spin off residual anhydrous methanol and SOCl 2 , washed the dark pink flocculent product with saturated aqueous sodium bicarbonate solution. Then it was extracted with ethyl acetate, dried, then suction filtered, and concentrated by rotary evaporation to obtain 35.9 g of dark brown oily liquid. Yield 95%. HPLC purity 99.6%.
[0038] (2) Synthesis of N-(3-methoxycarbonylphenyl)-thiourea:
[0039]
[0040] Add methyl 3-aminobenzoate (35.9g, 0.24mol...
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