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Indeno oxadiazine compound synthetic method

A technology of indenooxadiazine and a synthetic method, applied in directions such as organic chemistry, can solve problems such as low product yield and low purity, and achieve the effect of simplifying operation steps and facilitating industrial production

Inactive Publication Date: 2018-12-14
HUNAN GOFAR FINE CHEM IND TECH CO LDT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The above-mentioned traditional technology has disadvantages such as low product yield and low purity

Method used

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preparation example Construction

[0023] Synthetic method of 7-chloro-2,3,4a,5-tetrahydro-2-(benzyloxy)carbonylindeno(1,3,4)oxadiazine-4a-carboxylic acid methyl ester of one embodiment , including the following steps:

[0024] S110. Mix toluene, 5-chloro-2,3-dihydro-2-hydroxy-1-oxindene-2-carboxylic acid methyl ester, benzyl carbazate and toluenesulfonic acid at 60°C to 70°C ° C, react under vacuum conditions, remove water while reacting, and obtain the first reaction solution;

[0025] Wherein, the molar ratio of 5-chloro-2,3-dihydro-2-hydroxyl-1-indene-2-carboxylate, benzyl carbazate and toluenesulfonic acid is 1:(1.2~1.5 ): (0.1~0.3).

[0026] Further, the molar ratio of methyl 5-chloro-2,3-dihydro-2-hydroxy-1-oxindene-2-carboxylate, benzyl carbazate and toluenesulfonic acid is 1:1.2:0.1 .

[0027] Further, the vacuum degree of the reaction under vacuum condition is 0.085MPa-0.095MPa.

[0028] Further, the reaction time for the reaction under vacuum condition is 4-8 hours.

[0029] Further, the water ...

Embodiment 1

[0048] Add 50 g (96%, 0.20mol), 40g (0.24mol) of benzyl carbazate, 250g toluene and 3.5g (0.02mol) of anhydrous toluenesulfonic acid, heat up, vacuumize at 60°C, reflux and divide water, and keep warm for 8 hours to obtain The first reaction solution is ready for use.

[0049]Add 63 g (0.60 mol) of diethoxymethane and 150 g of toluene to a 1000 mL four-necked flask equipped with a stirrer, a thermometer and a rectifying tower, and gradually add the first reaction solution dropwise to the flask, and pass the rectification while reacting. The column removes the ethanol generated by the reaction, the temperature of the kettle is controlled at 120° C., and the temperature of the top of the rectification column is controlled at 70° C. to obtain the second reaction liquid.

[0050] After removing the toluenesulfonic acid and a small amount of impurities from the second reaction solution through a filter, the toluene and excess diethoxymethane were removed in a vacuum; methanol was ...

Embodiment 2

[0053] Add 50 g (96%, 0.20 mol), 50 g (0.3 mol) of benzyl carbazate, 250 g of toluene and 10.5 g (0.06 mol) of anhydrous toluenesulfonic acid, heat up, vacuumize at 70 ° C, reflux and divide water, and keep warm for 4 hours to obtain The first reaction solution is ready for use.

[0054] Add 105 g (1 mol) of diethoxymethane and 150 g of toluene to a 1000 mL four-necked flask equipped with a stirrer, a thermometer and a rectification tower, gradually add the first reaction solution dropwise to the flask, and pass through the rectification tower while reacting. The ethanol generated by the reaction was removed, the temperature of the kettle was controlled at 100° C., and the temperature of the top of the rectification column was controlled at 80° C. to obtain the second reaction liquid.

[0055] After removing the toluenesulfonic acid and a small amount of impurities from the second reaction solution through a filter, the toluene and excess diethoxymethane were removed in a vac...

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Abstract

The invention relates to an indeno oxadiazine compound synthetic method. The method comprises the following steps: mixing toluene, methyl 5-chloro-2,3-dihydro-2-hydroxy-1-oxo-inden-2-carboxylate, benzyl carbazate and methylbenzenesulfonic acid, performing a reaction under vacuum condition at 60 DEG C to 70 DEG C, and removing water while the reaction is carried out to obtain a first reaction solution; mixing toluene and diethoxymethane, adding the first reaction solution dropwise, and removing the ethanol while the reaction is carried out to obtain a second reaction solution; and separating and purifying the second reaction solution to obtain high-purity methyl 7-chloro-2,3,4a,5-tetrahydro-2-(benzyloxy)carbonyl indeno(1,3,4)oxadiazine-4alpha-carboxylate. The reaction yield is also high.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing indenoxadiazine compounds. Background technique [0002] Indoxacarb is a carbamate insecticide containing an oxadiazine structure developed by DuPont in 1992. The chemical name is (4aS)-7-chloro-2,3,4a,5-tetrahydro- Methyl 2-{methoxycarbonyl[(4-trifluoromethoxy)phenyl]carbamoyl}indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate . It is a chiral molecule, which is valued by the global pesticide industry because of its high efficiency, low toxicity, low residue, wide insecticidal spectrum and no carcinogenic, teratogenic and mutagenic effects. Its mechanism of action is to block the sodium ion channels in the nerve cells of pests, causing target pests to lose control, paralyze, unable to eat and finally die, thus protecting the target crops well. [0003] Methyl 7-chloro-2,3,4a,5-tetrahydro-2-(benzyloxy)carbonylindeno(1,3,4)oxadiazine-4a-carboxyla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D273/04
CPCC07D273/04
Inventor 陈儒贵
Owner HUNAN GOFAR FINE CHEM IND TECH CO LDT
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