N-(4-Bromobenzyl)-2-butyl-4-chloro-1H-imidazole-5-carboxyaldehyde synthesis
- Product Name:N-(4-Bromobenzyl)-2-butyl-4-chloro-1H-imidazole-5-carboxyaldehyde
- CAS Number:143722-29-6
- Molecular formula:C15H16BrClN2O
- Molecular Weight:355.66
83857-96-9
589-15-1
143722-29-6
Example 14 Synthesis of 1-(4-bromobenzyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde 2-n-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (111.9 g, 0.6 mol), p-bromobenzyl bromide (153.02 g, 0.6 mol), anhydrous potassium carbonate (103.5 g, 0.75 mol), and dry N,N-dimethylacetamide (900 mL) were mixed and the reaction was stirred for 4 hours at room temperature. After completion of the reaction, the reaction mixture was diluted with toluene (1.2 L) and water (1.8 L) and stirring was continued for 30 min. After standing and stratifying, the organic layer was separated and washed twice with 900 mL of water. The organic layer was dried with magnesium sulfate and filtered to remove the desiccant. The filtrate was concentrated and the residue was dried by vacuum pump overnight to give 191.71 g of the target product in 89.9% yield.
83857-96-9
492 suppliers
$8.00/10g
589-15-1
412 suppliers
$6.00/10g
143722-29-6
35 suppliers
$66.00/1g
Yield:143722-29-6 89.9%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl acetamide;water;toluene;
Steps:
14 2-n-Butyl-4-chloro-1-p-bromobenzyl-1H-imidazole-5-carboxaldehyde
EXAMPLE 14 2-n-Butyl-4-chloro-1-p-bromobenzyl-1H-imidazole-5-carboxaldehyde A mixture of 2-n-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (0.6 m=111.9 g), p-bromobenzylbromide (0.6 m=153.02 g), anhydrous potassium carbonate (0.75 m=103.5 g), and dry N,N-dimethylacetamide (900 mL) was stirred at room temperature for 4 hours. The mixture was diluted with 1.2L of toluene and 1.8L of water. After mixing for half an hour, the layers were separated. The organic layer was washed two more times with 900 mL portions of water, then dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated. The residual oil was pumped overnight to a weight of 191.71 g (89.9% yield).
References:
US5310928,1994,A