Method for preparing 1,3-dimethyladamantane

A technology of dimethyladamantane and dibromoadamantane, applied in 1 field, can solve problems such as being unsuitable for industrial production, and achieve the effects of improving product purity and mild process conditions

Inactive Publication Date: 2008-01-09
JIANGSU ANDY CHEM PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the production of tetramethyltitanium by this method needs to be carried out at a low temperature of -30°C, so it is not suitable for industrial production

Method used

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  • Method for preparing 1,3-dimethyladamantane
  • Method for preparing 1,3-dimethyladamantane
  • Method for preparing 1,3-dimethyladamantane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 1.1 mL (1.72 g, 11 mmol) of titanium tetrachloride and 0.13 g (1 mmol) of titanium trichloride to 100 mL of dimethylzinc (1M) in dichloromethane under rapid stirring below 0 °C aluminum. After continuing to stir for 1 hour, the resulting solution was slowly warmed to 10°C. A solution of 7.67 g (25.6 mmol) of 1,3-dibromoadamantane in dichloromethane (30 ml) was then slowly added dropwise. After stirring at this temperature for 3 hours the solution was poured into 30 ml of ice water. After acidification with concentrated hydrochloric acid, the organic phase was washed with sodium bicarbonate solution and water, dried with calcium chloride, and the solvent was removed. The crude product was isolated by distillation to give 3.2 g (75%) (B.p. 90-92° / 15 mmHg).

Embodiment 2

[0030] Add 1.1 mL (1.72 g, 11 mmol) of titanium tetrachloride and 0.13 g (1 mmol) of titanium trichloride to 100 mL of dimethylzinc (1M) in dichloromethane under rapid stirring below 0 °C aluminum. After continuing to stir for 1 hour, the resulting solution was slowly warmed to 5°C. A solution of 7.67 g (25.6 mmol) of 1,3-dibromoadamantane in dichloromethane (15 ml) was then slowly added dropwise. After stirring at this temperature for 3 hours the solution was poured into 30 ml of ice water. After acidification with concentrated hydrochloric acid, the organic phase was washed with sodium bicarbonate solution and water, dried with calcium chloride, and the solvent was removed. The crude product was isolated by rectification to obtain 3.5 g (82%) (B.p.90-92°C / 15mmHg).

Embodiment 3

[0032] To 100 ml of dimethylzinc (1M) in dichloromethane, 1.1 ml (1.72 g, 11 mmol) of titanium tetrachloride and 0.26 g (2 mmol) of trichloride were added below 0°C with rapid stirring. aluminum. After continuing to stir for 1 hour, the resulting solution was slowly warmed to 10°C. A solution of 7.67 g (25.6 mmol) of 1,3-dibromoadamantane in dichloromethane (15 ml) was then slowly added dropwise. After stirring at this temperature for 3 hours the solution was poured into 30 ml of ice water. After acidification with concentrated hydrochloric acid, the organic phase was washed with sodium bicarbonate solution and water, dried with calcium chloride, and the solvent was removed. The crude product was isolated by rectification to obtain 3.4 g (80%) (B.p.90-92° / 15 mmHg).

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Abstract

This invention discloses a method for producing 1,3-dimethyladamantane, comprising: (1) add titanium tetrachloride and aluminium trichloride to zinc dimethyl dichloromethane solution, mix thoroughly at -10-10Deg C, then at 5-25Deg C, add dropwise 1,3-dibromideadamantane dichloromethane solution, stirring reaction for 1-10 hours; (2) hydrolyze the reaction mixture produced from the procedure(1) with ice water and hydrochloric acid, followed by extraction, drying and distillation. During the process of this invention, since it adds in aluminium trichloride, it changes the reaction activity of the zinc dimethyl mixture, thus it can improve the reaction required temperature from -30Deg C to -10-10Deg C, which improves the yield and purity of the product, and makes the process conditions more mild, very suitable for industrialization.

Description

technical field [0001] The invention relates to a preparation method of 1,3-dimethyladamantane. Background technique [0002] 1,3-Dimethyladamantane is an important intermediate for the preparation of adamantane drugs. At present, the preparation of 1,3-dimethyladamantane mainly contains the following methods: [0003] Method 1, 1,3-(dichloromethyl)adamantane reduction preparation (K.Landa, Collect.Czech.Chem.Commun.1959, 24, 1320-1323.) [0004] [0005] The raw material 1,3-(dichloromethyl)adamantane used in this method is difficult to synthesize, has high cost, harsh reaction conditions, and needs to use flammable ether as a solvent, so it has no practical production value. [0006] Method 2. Preparation by reduction of 1,3-(dibromomethyl)adamantane (K.Landa, Collect.Czech.Chem.Commun.1959, 24, 1320-1323.) [0007] [0008] The raw material 1,3-(dibromomethyl)adamantane used in this method is difficult to synthesize and the cost is relatively high. A large amoun...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/615C07C2/88
Inventor 康宏杰黎占亭杜娟冯代军胡强陈找根
Owner JIANGSU ANDY CHEM PHARMA CO LTD
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