ChemicalBook CAS DataBase List 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE

1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE synthesis

10synthesis methods

Product Name:1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
CAS Number:173035-10-4
Molecular formula:C21H29ClN2
Molecular Weight:344.92

122-51-0

N,N'-bis(2,4,6-trimethylphenyl)ethane-1,2-diamine,dihydrochloride

258278-23-8

1,3-BIS(2,4,6-TRIMETHYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE

173035-10-4

Sodium borohydride (NaBH4, 4.24 g, 112.1 mmol) was slowly added to a solution of N,N'-bis(2,4,6-trimethylphenyl)ethylenediamine hydrochloride (8.0 g, 27.3 mmol) in tetrahydrofuran (THF, 100 mL) at 0 °C. Subsequently, concentrated hydrochloric acid (HCl, 4.5 mL, 2 eq.) was added dropwise over 30 min. After the dropwise addition, the reaction mixture was continued to be stirred at 0 °C for 20 min. Next, 3M hydrochloric acid (250 mL) was carefully added to the reaction flask at 0°C and the mixture was stirred for 1 hour, during which time the temperature was allowed to naturally rise to room temperature. Upon completion of the reaction, the white precipitate was collected by filtration and washed sequentially with water (200 mL) and 5% acetone-ether mixture (150 mL). The resulting product (9.4 g, 93% yield) was a white solid, which was dried under vacuum and prepared for use. The above obtained hydrochloride (8.5 g, 23 mmol) was suspended in triethyl orthoformate (HC(OEt)3, 35 mL, 162 mmol) and 2 drops of formic acid (HCO2H, ca. 1 mol%) was added as catalyst. The reaction mixture was heated to 120 °C and maintained for 5 hours under argon (Ar) protection. At the end of the reaction, it was cooled to room temperature and hexane (200 mL) was added to precipitate the product. After stirring for 1 hour, the white precipitate was collected by filtration, washed with hexane (200 mL) and dried under vacuum to give the final 1,3-bis(2,4,6-trimethylphenyl)imidazole hydrochloride (IMesH2-HCl, 7.6 g, 96% yield).

64-18-6 Synthesis

64-18-6
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258278-23-8
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173035-10-4
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Yield:173035-10-4 80%

Reaction Conditions:

with orthoformic acid triethyl ester at 23 - 130;Inert atmosphere;

Steps:

1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride5
A mixture of 1.12 g (3.03 mmol) of N,N'-bis-(2,4,6-trimethylphenylamino)ethane dihydrochloride, 10mL of triethyl orthoformate, and one drop of 96% formic acid was heated in a distillation apparatus until the ethanol distillation ceased. The temperature of the reaction mixture reached 130 ^oC. Uponcooling to 23 ^oC, a colorless solid precipitated which was collected by filtration and dried in vacuo.

References:

Zeng, Wei;Wang, Enyu;Qiu, Rui;Sohail, Muhammad;Wu, Shaoxiang;Chen, Fu-Xue [Journal of Organometallic Chemistry,2013,vol. 743,p. 44 - 48] Location in patent:supporting information

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122-51-0 Synthesis

122-51-0
518 suppliers
$10.00/5ml

258278-23-8
10 suppliers
inquiry

173035-10-4
190 suppliers
$43.00/500mg

References

122-51-0 Synthesis

122-51-0
518 suppliers
$10.00/5ml