α-(2,3-Dimethylphenyl)-1-(trityl)-1H-imidazole-4-methanol Chemical Properties

Melting point:

180 - 184°C

Boiling point:

616.0±50.0 °C(Predicted)

Density 

1.09±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly, Heated)

form 

Solid

pka

13.08±0.20(Predicted)

color 

White to Off-White

α-(2,3-Dimethylphenyl)-1-(trityl)-1H-imidazole-4-methanol Usage And Synthesis

Chemical Properties

White Solid

Uses

α-(2,3-Dimethylphenyl)-1-(trityl)-1H-imidazole-4-methanol is an Intermediate in the production of Medetomidine

Synthesis

1. 11.5 g (60.2 mmol) of 1-bromo-2,3-dimethylbenzene was dissolved in 200 mL of anhydrous tetrahydrofuran (THF) in a dry reaction flask. 2. a mixed system consisting of 1.5 g (61.7 mmol) of magnesium strips, 0.05 g of iodine, and 50 mL of anhydrous THF was slowly added dropwise to initiate the preparation of Grignard's reagent. 3. After dropwise addition, the reaction system was heated to reflux and maintained at reflux for 1 hour to ensure complete reaction. 4. After completion of the reaction, the system was cooled to room temperature to obtain a solution of 2,3-dimethylphenylmagnesium bromide Grignard reagent. 5. In another dry reaction flask, 17.5 g (50.2 mmol) of 1-tritylimidazole-4-carbaldehyde was dissolved in 225 mL of anhydrous THF and this solution was cooled to 0 °C. The reaction was carried out at 0 °C. 6. The Grignard reagent solution prepared in step 4 was slowly added to the aldehyde solution at 0 °C, with controlled drop acceleration to maintain the reaction temperature. 7. After the addition is complete, the reaction mixture is stirred at room temperature for 1.5 hours to complete the nucleophilic addition reaction. 8. The reaction was quenched using saturated aqueous ammonium chloride solution and then most of the THF was removed by concentration under reduced pressure. 9. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product. 10. The crude product was dissolved in dichloromethane and after removing most of the solvent by concentration under reduced pressure, the residue was cooled to -5 °C and kept for 1 hour to promote crystallization. 11. The crystals were collected by filtration, washed with cold dichloromethane and dried to give 12.4 g of (2,3-dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanol in 53.9% yield.

References

[1] Patent: CN108147999, 2018, A. Location in patent: Paragraph 0162; 0163
[2] Synthetic Communications, 1996, vol. 26, # 8, p. 1585 - 1593
[3] Journal of the Iranian Chemical Society, 2017, vol. 14, # 8, p. 1735 - 1739

α-(2,3-Dimethylphenyl)-1-(trityl)-1H-imidazole-4-methanol(176721-01-0)Related Product Information

• 2,3-Dimethylbenzoic acid
• Medetomidine Impurity 2
• Dexmedetomidine-007
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• Medetomidine Impurity 14
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• IMIDAZOLE-1-SULFONIC ACID DIMETHYL AMINE
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• 2,3-DIMETHYLACETOPHENONE
• Medetomidine Impurity 3
• 3,4-Dimethylbromobenzene
• 2,3-Dimethylbenzyl chloride
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