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Synthesis of 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane

A technology of chloromethyl propane and a synthesis method, which is applied in the field of synthesis of 1,1-dibromo-2,2-bicyclopropane, can solve the problems of harsh conditions, difficulty in amplification and high cost, and achieves improved yield and reduced instantaneous Heat release, the effect of simple preparation method

Active Publication Date: 2021-06-01
ASTATECH CHENGDU BIOPHARM CORP
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is that the existing method for synthesizing 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane has low yield, high cost, and difficult amplification. The synthetic method of bromo-2,2-bis(chloromethyl)cyclopropane solves the problem of low yield and harsh conditions of existing methods for synthesizing 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane question

Method used

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  • Synthesis of 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane
  • Synthesis of 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane
  • Synthesis of 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane

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Embodiment 1

[0037] The synthetic method of 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane of the present invention comprises the following steps: 2-amino-2-hydroxymethylpropane-1,3-diol and thionyl chloride Chlorine substitution reaction to obtain (1,3-dichloro-2-(chloromethyl)propan-2-yl) aminosulfone ketone; then hydrolysis by concentrated sulfuric acid aqueous solution to obtain 1,3-dichloro-2-chloromethyl Propan-2-amine sulfate; followed by salt solution under alkaline conditions, and ring closure to obtain 2,2-bis(chloromethyl)aziridine; then react with sodium nitrite to obtain 3-chloro-2-chloro Methylprop-1-ene; Finally, it reacts with tribromomethane under basic conditions to generate 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane. In the present invention, 1,1-dibromo-2,2-bis(chloro Methyl) cyclopropane, the reaction formula that synthetic method involves is as figure 1 shown.

Embodiment 2

[0039] Based on embodiment 1, the specific synthetic method of the present invention is as follows:

[0040] Synthesis of step A, (1,3-dichloro-2-(chloromethyl)propane-2-yl)aminosulfone ketone: 5kg2-amino-2-hydroxymethylpropane-1,3-diol is dissolved in In toluene, add 25 kg of thionyl chloride under temperature control at 20-40 ° C, add 0.653 kg of pyridine after cooling down to 10-15 ° C, react at room temperature for 2 hours, and gradually increase the temperature to 105-110 ° C for 10 hours; after the reaction, 9.18 Toluene solution of kg (1,3-dichloro-2-(chloromethyl)propan-2-yl)aminosulfone, yield 100%.

[0041] Synthesis of step B, 1,3-dichloro-2-chloromethylpropan-2-amine sulfate: 9.18kg (1,3-dichloro-2-(chloromethyl)propane-2- Base) the toluene solution of aminosulfone ketone is controlled at a temperature not exceeding 25°C, and water and concentrated sulfuric acid aqueous solution are added; the temperature is raised to 85-95°C and reacted for 15-22 hours; , the aq...

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Abstract

The invention discloses a synthesis method of 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane, comprising the following steps: 2-amino-2-hydroxymethylpropane-1,3-diol and dichloro Sulfoxide carries out chlorine substitution reaction and obtains (1,3-dichloro-2-(chloromethyl) propane-2-yl) aminosulfone ketone; (1,3-dichloro-2-(chloromethyl) propane-2 - Base) aminosulfone ketone is hydrolyzed by concentrated sulfuric acid aqueous solution to obtain 1,3-dichloro-2-chloromethylpropane-2-amine sulfate; 1,3-dichloro-2-chloromethylpropane-2-amine Sulphate is desalted under alkaline conditions, and the ring is closed to obtain 2,2-bis(chloromethyl)aziridine; 2,2-bis(chloromethyl)aziridine is reacted with sodium nitrite to obtain 3‑Chloro‑2‑chloromethylprop‑1‑ene; 3‑Chloro‑2‑chloromethylprop‑1‑ene reacts with bromoform under basic conditions to form 1,1‑dibromo‑2,2‑ Bis(chloromethyl)cyclopropane. The preparation method of the invention is simple and can be scaled up for production.

Description

technical field [0001] The invention relates to an organic synthesis method, in particular to a synthesis method of 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane. Background technique [0002] 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane is the core intermediate of the clinical candidate bicyclo(1.1.1)pentan-1-amine. Due to the shortage of bicyclo(1.1.1)pentan-1-amine due to a large number of purchases on the market, 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane is just a quick synthesis of bicyclo(1.1.1. 1) The core intermediate of pent-1-amine. However, the current schemes for the synthesis of the core fragment 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane have problems such as low yield and difficult amplification. [0003] Lynchand K.M. and DaileyW.P. (referring to J.Org.Chem.1995,60,4666) utilize pentylene glycol as raw material, adopt the route shown in following reaction formula to prepare 1,1-dibromo-2,2-bis( Chloromethyl) cyclopropane. The process step of this ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/10C07C209/00C07C211/15C07D203/08C07C17/35C07C21/09C07C17/278C07C23/04
CPCC07C17/278C07C17/35C07C209/00C07C381/10C07D203/08C07C2601/02C07C211/15C07C21/09C07C23/04
Inventor 王银哈雷克瑞什南·科拉图尔·纳拉西姆汉·昆奇塔帕达姆拉格海温德·拉奥·莫莎拉赵振宇徐辉郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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