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

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H319Causes serious eye irritation

H361Suspected of damaging fertility or the unborn child

H362May cause harm to breast-fed children

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

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

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