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Process for synthesizing N-caprylyl benzotriazole

A technology of benzotriazole and synthesis process, which is applied in the direction of organic chemistry, can solve the problems of increased production cost, increased environmental pollution, complex post-processing, etc., and achieves the effects of low cost, high purity, and reduced production cost

Inactive Publication Date: 2016-01-13
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] N-octanoylbenzotriazole can be used as an important cheap acylating reagent in organic synthesis, but when synthesizing the acylating reagent N-octanoylbenzotriazole, there are few methods in the literature, and currently The route of synthesizing N-octanoyl benzotriazole mainly has the following disadvantages: 1) use octanoic acid and benzotriazole as raw materials to react, and benzotriazole needs to be activated into an active intermediate, which is then reacted with octanoic acid to generate N-octanoyl benzotriazole, causes production cost to improve like this, and yield is lower, and aftertreatment is complicated, increases environmental pollution; Under the reaction with benzotriazole to generate N-octanoylbenzotriazole, the subsequent treatment needs to be purified by chromatography column, and the more expensive iodine and triphenylphosphine are used

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Dissolve benzotriazole (11.9Kg, 100mol) in 60 liters of dry 1,2-dichloroethane, add triethylamine (15.2Kg, 150mol), then heat up to 30°C, add octanoyl chloride dropwise (19.5Kg, 120mol), the dropping time is 4 hours, and the temperature is controlled not to exceed 45°C during the dropping process. After the dropping is completed, react at room temperature for 8 hours, then wash with water (20L×2), and use 3% hydrogen The sodium oxide solution adjusted the pH value to 9, and then washed with water (20L). rate 99%). 1 HNMR (CDCl 3 ,300MHz)δ:8.26-8.29(m,1H),8.08-8.11(m,1H),7.60-7.66(m,1H),7.45-7.51(m,1H),3.38-3.43(m,2H), 1.84-1.94 (m, 2H), .1.21-1.35 (m, 8H), 0.81-0.89 (m, 3H).

Embodiment 2

[0022] Add 57 liters of the recovered solvent 1,2-dichloroethane to 5 kg of anhydrous sodium sulfate, stir and dry for 6 hours, filter and set aside for reaction. Dissolve benzotriazole (11.9Kg, 100mol) in 1,2-dichloroethane recovered by drying, add 5 liters of dry 1,2-dichloroethane, add triethylamine (15.2Kg , 150mol), then heated up to 30°C, added dropwise octanoyl chloride (19.5Kg, 120mol), the dropwise addition time was 4 hours, the temperature was controlled not to exceed 45°C during the dropwise addition, after the dropwise addition, reacted at room temperature for 8 hours , then wash with water (20L×2), adjust the pH value to 9 with 3% sodium hydroxide solution, then wash with water (20L), after standing for separation, concentrate under reduced pressure, and recover the solvent 1,2-dichloroethane 58 liters, a light yellow oily product (24.0Kg, yield 98%) can be obtained. The yield of applied solvent is basically the same as that of fresh solvent. This shows that the...

Embodiment 3

[0024] Dissolve benzotriazole (11.9Kg, 100mol) in dry ethyl acetate (36L), add triethylamine (15.2Kg, 150mol), then raise the temperature to 30°C, add octanoyl chloride (19.5Kg, 120mol) dropwise , the dropping time is 4 hours, and the temperature is controlled not to exceed 45°C during the dropping process. After the dropping is completed, react at room temperature for 8 hours, then wash with water (15L×2), and adjust the pH value with 3% sodium hydroxide solution 9, then washed with water (15 L), left to stand and separated, concentrated under reduced pressure, recovered 30 liters of ethyl acetate as a solvent, and obtained a light yellow oily product (24.2Kg, yield 99%). 1 HNMR (CDCl 3 ,300MHz)δ:8.26-8.29(m,1H),8.08-8.11(m,1H),7.60-7.66(m,1H),7.45-7.51(m,1H),3.38-3.43(m,2H), 1.84-1.94 (m, 2H), .1.21-1.35 (m, 8H), 0.81-0.89 (m, 3H).

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Abstract

The invention relates to a process for synthesizing N-caprylyl benzotriazole. The process comprises the following steps: dissolving benzotriazole and alkali into a dry solvent, dropping caprylyl chloride at 20-120 DEGC for 2-6 hours, after dropping, keeping the temperature of 20-120 DEGC to react for 3-15 hours, cooling to the room temperature, washing twice with water, adjusting the pH value to 7-10 by using a 1-10% sodium hydroxide solution, washing with water once again, leaving to stand to layer, performing depressurized concentration, and recycling the solvent, thereby obtaining a target product; applying the received solvent mechanically to next reaction after being dried, wherein the mole ratio of benzotriazole and alkali to caprylyl chloride is 1:(1.0-2.5):(1.0-2.0), and the volume mass ratio of the dried solvent to benzotriazole is (1-10):1. Compared with the prior art, the process is not only good in product quality, stable to operate, small in amount of wastes and low in production cost, but also high in purity and high in yield.

Description

[technical field] [0001] The invention relates to a synthesis process of N-octanoylbenzotriazole. [Background technique] [0002] N-octanoylbenzotriazole can be used as an important cheap acylating reagent in organic synthesis, but when synthesizing the acylating reagent N-octanoylbenzotriazole, there are few methods in the literature, and currently The route of synthesizing N-octanoyl benzotriazole mainly has the following disadvantages: 1) use octanoic acid and benzotriazole as raw materials to react, and benzotriazole needs to be activated into an active intermediate, which is then reacted with octanoic acid to generate N-octanoyl benzotriazole, causes production cost to improve like this, and yield is lower, and aftertreatment is complicated, increases environmental pollution; Next, react with benzotriazole to generate N-octanoylbenzotriazole, and the subsequent treatment needs to be purified by chromatographic column, and more expensive iodine and triphenylphosphine ar...

Claims

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Application Information

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IPC IPC(8): C07D249/18
CPCC07D249/18
Inventor 吴岳林索奇吴范宏
Owner SHANGHAI INST OF TECH
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