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A kind of preparation method of 1-bromoadamantane

A technology of adamantane and bromination, applied in the field of preparation of 1-bromoadamantane, which can solve the problems of serious environmental pollution, complicated operation, and large equipment corrosion

Active Publication Date: 2021-08-20
KENTE CATALYSTS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned methods all use bromine, which has relatively large corrosion to equipment, serious environmental pollution, and relatively complicated operations.

Method used

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  • A kind of preparation method of 1-bromoadamantane
  • A kind of preparation method of 1-bromoadamantane
  • A kind of preparation method of 1-bromoadamantane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 1.36g of adamantane (0.01mol), 1.43g (0.005mol) of dibromohydantoin (divided into 3 batches) into a 50ml three-necked flask, then add 25ml of dichloromethane, stir at room temperature for 30 minutes, and heat to the boiling point °C reflux. After reacting for 24 hours, turn off the heating and stirring, cool to room temperature, add saturated sodium bisulfite solution in an ice bath until the bromine yellow color disappears, stir for 15 minutes, remove the precipitated solid by filtration, separate the filtrate to obtain an organic phase, wash with 100 mL of water three times, dry, and concentrate to obtain crude product. The crude product was recrystallized from methanol to obtain 1.47g of white 1-bromoadamantane crystals with a yield of 68%. The melting point is 115.2-117.3°C. Replacement examples 1-1 to 1-8:

[0026] The preparation method is the same as in Example 1, the difference is that the type of solvent is adjusted to test its influence on the reaction,...

Embodiment 2

[0032] Add 1.36g of adamantane (0.01mol), 1.43g (0.005mol) of dibromohydantoin (divided into 3 batches) into a 50ml three-necked flask, then add 25ml of chloroform, stir at room temperature for 30 minutes, and heat to 30°C reflow. After reacting for 24 hours, turn off the heating and stirring, cool to room temperature, add saturated sodium bisulfite solution in an ice bath until the bromine yellow color disappears, stir for 15 minutes, remove the precipitated solid by filtration, separate the filtrate to obtain an organic phase, wash with 100 mL of water three times, dry, and concentrate to obtain crude product. The crude product was recrystallized from methanol to obtain 0.94g off-white 1-bromoadamantane crystals with a yield of 44%. The melting point is 116.0-116.8°C. Replacement examples 2-1 to 2-15:

[0033] The preparation method is the same as in Example 2, the difference is that the reaction temperature, reaction time, solvent (chloroform) usage amount, adamantane (1...

Embodiment 3

[0037] Embodiment 3: amplification reaction (5 times)

[0038] Add 6.81g of adamantane (0.05mol), 14.30g (0.05mol) of dibromohydantoin (divided into 3 batches) into a 250ml three-necked flask, then add 125ml of chloroform, stir at room temperature for 30 minutes, and heat to 65°C reflow. After reacting for 30 hours, turn off the heating and stirring, cool to room temperature, add saturated sodium bisulfite solution in an ice bath until the bromine yellow color disappears, stir for 15 minutes, remove the precipitated solid by filtration, separate the filtrate to obtain an organic phase, wash with 500 mL of water three times, dry, and concentrate to obtain crude product. The crude product was recrystallized from methanol to obtain 9.61 g of off-white crystals of 1-bromoadamantane with a yield of 89%. The melting point is 114.6-115.0°C.

[0039] Can draw in conjunction with above embodiment:

[0040] 1. The present invention uses 1,3-dibromo-5,5-dimethylhydantoin as a bromina...

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Abstract

The invention discloses a preparation method of 1-bromoadamantane, which is characterized in that: adamantane is used as a starting material, and 1,3-dibromo-5,5-dimethylhydantoin is a green brominated reagent. A mild bromination reaction was carried out in chloroform to obtain the target product with high purity. The synthesis process of the invention is environmentally friendly, easy to operate, low in price and easy to obtain, and suitable for large-scale industrial production.

Description

Technical field: [0001] The invention belongs to the technical field of medicine synthesis, and specifically refers to a preparation method of 1-bromoadamantane. Background technique: [0002] 1-Bromoadamantane (1-Bromoadamantane) is an important intermediate in the synthesis of amantadine hydrochloride, and amantadine hydrochloride is an antidrug, which is very effective in treating Asian A2 influenza. There are few manufacturers of this kind of medicine in the domestic pharmaceutical industry, and foreign medicines are expensive, and the supply exceeds demand in the market. Therefore, it has a good market prospect and huge economic and social benefits. Most of the synthetic methods in current related reports are brominated by bromine, as in J.Am.Soc.Chem.1980,102,712, Barfield, M. reported that the method of synthesizing 1-bromoadamantane is adamantane in bromine After the reaction is completed, it is poured into carbon tetrachloride for treatment. The excess bromine is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/10C07C23/38
CPCC07C17/10C07C2603/74C07C23/38
Inventor 王新伟李青山施旭升董柱永吴尖平王丹燕沈永淼
Owner KENTE CATALYSTS INC
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