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CAS No. : | 32673-41-9 | MDL No. : | MFCD00012697 |
Formula : | C4H7ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WFNASTYGEKUMIY-UHFFFAOYSA-N |
M.W : | 134.56 | Pubchem ID : | 122926 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 31.68 |
TPSA : | 48.91 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.11 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.01 |
Log Po/w (WLOGP) : | 0.55 |
Log Po/w (MLOGP) : | -0.94 |
Log Po/w (SILICOS-IT) : | 0.9 |
Consensus Log Po/w : | 0.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.08 |
Solubility : | 11.3 mg/ml ; 0.0837 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.59 |
Solubility : | 34.7 mg/ml ; 0.258 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.98 |
Solubility : | 14.0 mg/ml ; 0.104 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.38 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.5% | With hydrogenchloride; ammonium cerium (IV) nitrate; sodium ethanolate In ethanol; acetonitrile at 60℃; for 8 h; | A mixture of acetonitrile and ethanol in a volume ratio of 2: 1 was added to the reactor,100 mmol of 1,3-dihydroxyacetone and 200 mmol of formaldehyde were dissolved in an organic solvent,100 mmol of cerium ammonium nitrate was added,Under normal pressure 60 conditions,Adding sodium ethoxide to adjust the pH to 10,15 mmol of catalyst was added,Stirring reaction 8h, obtained 4-hydroxymethyl imidazole,After completion of the reaction,Dropping concentrated HCl,Adjust pH = 2,filter,The filtered solid,Washed with saturated brine,Recrystallization from ethanol,Dried in vacuo to give the product 4-hydroxymethylimidazole hydrochloride.The purity of the prepared 4-hydroxymethylimidazolidine hydrochloride was 98.2percentThe yield was 87.5percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With thionyl chloride In toluene | (A) 4-(Chloromethyl)imidazole hydrochloride (1) To a solution of 20 ml of toluene containing 2 ml of thionyl chloride was added 700 mg of 4-(hydroxymethyl)imidazole hydrochloride. The reaction mixture was heated to the refluxing temperature of the solvent for 3 hours, cooled and concentrated to dryness under reduced pressure. The title compound was obtained as a white solid (790 mg, 99percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With thionyl chloride; In toluene; | (A) 4-(Chloromethyl)imidazole hydrochloride (1) To a solution of 20 ml of toluene containing 2 ml of thionyl chloride was added 700 mg of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong>. The reaction mixture was heated to the refluxing temperature of the solvent for 3 hours, cooled and concentrated to dryness under reduced pressure. The title compound was obtained as a white solid (790 mg, 99% yield). |
96.5% | With thionyl chloride; | EXAMPLE I To thionyl chloride (170 ml, 2.35 m) stirred at room temperature there was added portion-wise over a ten minute period with exclusion of moisture, 64 g (0.48 m) of <strong>[32673-41-9]4-hydroxymethylimidazole hydrochloride</strong>. With each addition vigorous evolution of gas occurred and occasional cooling by ice/water bath was necessary to keep the temperature below 30 C. The resulting greenish solution was stirred at 30 C. for an additional ten minutes until the gas evolution subsided. The temperature was then raised to 55+-5 C. for forty minutes during which time a thick gelatinous precipitate formed. The reaction mixture was cooled and excess thionyl chloride removed under reduced pressure at 30 C. The yellow residue was triturated with 100 ml of ether, collected and washed four times with 50 ml of ether. The product, a very pale yellow powder, was dried in a stream of air to give 70.88 g (96.5% yield) of 4-chloromethylimidazole hydrochloride m.p. 145-6 C. which was stored under refrigeration. C4 H6 N2 Cl2 requires 31.40% C, 3.95% H, 18.31% N and 46.34% Cl. Elemental analysis found 31.30% C, 4.01% H, 18.34% N and 47.17% Cl. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
538 mg starting material (4 mmol) was dissolved in ~ 4 ml methanol and 500 mg NaHCO3 (6 mmol) was added. The tube was occasionally stirred for 60 min, alternatively at 4 C and at warm water temperature. CO2 was allowed to escape from the glass tube. The mix was divided across several Eppendorf tubes and subjected to Speedvac treatment for 1 hour. Residues were white solids with light-yellow sirupy liquids. Chloroform/methanol mix 1:1 was added to the tubes with subsequent gentle warming and stirring. NaHCO3 was separated by centrifugation of the combined fractions at 3500 rpm for 5 min. Clear supernatant was kept overnight at -20 C to allow the precipitation of additional NaHCO3. Then, the solution was cleared by filtration and evaporated to dryness with a Rotavapor device. The residue was taken up in 20 ml dioxane with magnetic stirring and 4.4 mg MnO2 (activated; for synthesis) was added in the same flask. The residue may not have been dissolved completely in first instantion. The mix was refluxed for 2 hours on a paraffin oil bath. The warm solution was filtered and MnO2 was washed once with warm dioxane. Dioxane was evaporated with the Rotavapor yielding a white and yellow fine cristalline solid. Crystallization was carried out in methanol repeated times. Small volumes of methanol were required, because the residue dissolved well in methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In tetrahydrofuran; dichloromethane; ethyl acetate; | The starting material alcohol for the acylation was obtained as follows, using a procedure from European Patent Application, Publication Number 284 174. To a solution of 4-imidazolylcarbinol hydrochloride (1.01 g) in dry dichloromethane (5 mL) was added pyridine (1.82 mL) and di-tert-butyl dicarbonate (2.46 g). The resulting solution was stirred overnight, evaporated and resuspended/dissolved in 100 mL of ethyl acetate/tetrahydrofuran (9:1). The organic phase was washed (three times with water, brine), dried, evaporated and dried under high vacuum to give 1-tert-butoxycarbonylimidazol-4-ylcarbinol as a colorless oil; TLC: Rf =0.30, dichloromethane:ethyl acetate:methanol (50:49:1); MS: m/z=199(M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Step 8.a. 4-Hydroxymethyl-1-triphenylmethyl-imidazole 4-Hydroxymethylimidazole hydrochloride (compound xiii where R2 is H) (2.50 g, 18.6 mmol) and Et3N (2.59 ml, 18.6 mmol) were combined in DMF (30 ml) and stirred at room temperature.. A solution of chlorotriphenylmethane (5.19 g, 18.6 mmol) in DMF (25 ml) was added dropwise at room temperature and the resulting mixture was stirred at room temperature for about 23 hours and then poured into ice water (300 ml).. The product was filtered off, washed with cold water (75 ml) and triturated with p-dioxane (30 ml).. The product was filtered off and dried under reduced pressure to yield product (4.96 g, 78%). NMR (300MHZ, DMSO-d6, 30C) 7.3-7.5 (9H, m), 7.25-7.35 (1H, d), 7.0-7.2 (6H, m), 6.7-6.75 (1H, s), 4.15-4.2 (2H, m). | |
With triethylamine; In N,N-dimethyl-formamide; | Step A 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid. |
With triethylamine; In N,N-dimethyl-formamide; | Step A: Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenyl-methane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenyl-methane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid. | |
With triethylamine; In N,N-dimethyl-formamide; | Step J Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A: Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A 4-(Hydroxymethyl)-1-(triphenylmethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A 4-(Hydroxymethyl)-1-(triphenylmethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenyl-methane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title product as a white. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vaculo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A 1-Triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step B 1-Triphenylmethyl-4-(hydroxymethyl)imidazol To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl) imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 ml, of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step F 4-Hydroxymethyl-1-triphenylmethylimidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature is added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF is added dropwise. The reaction mixture is stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product is slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which is sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title compound as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole (2) To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide 2 as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title compound as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step E 1-Triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step J Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vccuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 ml) at room temperature was added triethylamine (90.6 ml, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in of DMF (500 ml) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A 1-Triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In dichloromethane; | (a) Triphenylmethyl chloride (2.78 g) was added to <strong>[32673-41-9]4-hydroxymethylimidazole hydrochloride</strong> (1.34 g) and triethylamine (2.8 ml) in dichloromethane (20 ml) stirred at 0 C. under an atmosphere of argon. The mixture was stirred for 18 hours and the insoluble solid was collected by filtration. The solid was washed well with water and dried under high vacuum to give 4-hydroxymethyl-1-triphenylmethyl-imidazole (B) as a white solid (2.4 g); NMR (90 MHz, d6 -DMSO): 4.3 (d, 2H), 4.8 (br t, 1H), 6.7 (S, 1H), 7.0-7.5 (complex m, 16H). | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In dichloromethane; at 20℃; for 18.0h; | (iii) (1-trityl-1H-imidazol-4-yl)methanol Trityl chloride (2.1 g) was added to a mixture of 4-hydroxymethyl imidazole hydrochloride (1.0 g) and triethylamine (3.1 ml) in DCM (25 ml) at RT. Further DCM (20 ml) was added and the mixture stirred for 18 h. The precipitate was filtered, washed with water and then ether to give the subtitle compound (2.0 g). 1H NMR DMSO-d6: delta 7.44-7.36 (9H, m), 7.29 (1H, s), 7.10-7.08 (6H, m), 6.72 (1H, s), 4.87 (1H, t), 4.33 (2H, d). | |
Step A: 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | ||
With triethylamine; In N,N-dimethyl-formamide; | Step A: 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole. To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 ml) at room temperature was added triethylamine (90.6 ml, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in of DMF (500 ml) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step. | |
With triethylamine; In N,N-dimethyl-formamide; | Step B 4-Hydroxymethyl-1-triphenylmethylimidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature is added triethylamine (90.6 mL, 650 mmol). A white solid precipitates from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF is added dropwise. The reaction mixture is stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product is slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product which is sufficiently pure for use in the next step. |
Yield | Reaction Conditions | Operation in experiment |
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43% | With triethylamine; for 16.0h;Heating / reflux; | To a solution of ethyl 3-ethoxy-7-fluoro-6-nitroquinoxaline-2-carboxylate (6.90 g, 22.3 mmol) in acetonitrile (70 ml) were added dropwise <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (15.1 g, 112 mmol) and successively triethylamine (23.4 ml, 168 mmol) under shading, and the mixture was refluxed for 16 hours. After cooling, methylene chloride was added to the reaction mixture, which was washed with water. The aqueous layer was extracted with methylene chloride, which was combined with foregoing organic layer. After dried over anhydrous sodium sulfate, solvent was distilled off. The residue obtained was purified by means of silica gel column chromatography [ethyl acetate] to obtain 3.69 g of the the title compound as brown power. Yield 43%. Moreover, 2.15 g of ethyl 3-ethoxy-7-fluoro-6-nitroquinoxaline-2-carboxylate were recovered. Yield 31%. 1H-NMR(CDCl3,delta):1.47(3H,t,J=7.1 Hz),1.53(3H,t,J=7.1 Hz), 4.55(2H,q,J=7.2 Hz),4.66(2H,q,J=7.2 Hz),4.71(2H,s),7.09(1H,s), 7.68(1H,d,J=1.5 Hz),8.15(1H,s),8.43(1H,s). |
Yield | Reaction Conditions | Operation in experiment |
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67% | With N-ethyl-N,N-diisopropylamine; at 120℃; for 12.0h; | 3,4-Difluoronitrobenzene (2 grams, 12.5 mmol) and 4- (hydroxymethyl)-imidazole hydrochloride (1.86 grams, 13.8 mmol) were taken together in N, N-diisopropylethylamine (25 mL) and heated to 120 C for 12 hours. Two layers were formed after the reaction mixture was allowed to cool to room temperature. Upper layer was decanted and ethyl acetate (500 mL) was added to the remaining portion. The ethyl acetate layer was washed with water followed by brine and dried over sodium sulfate. Evaporation of solvent yielded the tilte compound as brown solid (2 grams, 67%). IH NMR (DMSO-D6) : 5 8.43 (dd, J=2. 2&11 Hz, 1H), 8. 31-8. 10 (m, 2H), 7.97 (t, J=8. 3 Hz, 1H), 7.54 (s, 1H), 5.09 (bs, 1H), 4.44 (d, J=4. 3 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
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With 8-quinolinol; potassium carbonate;copper(l) iodide; In dimethyl sulfoxide; at 130℃; | Example 29 5-chloro-N-((1-(3-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (40) A mixture of <strong>[147808-02-4]2,5-diiodofluorobenzene</strong> II-4 (2.50 g, 7.18 mmol), 4-hydroxymethylimidazole hydrochloride (0.967 g, 7.18 mmol), 8-hydroxyquinoline (0.104 g, 0.717 mmol) and K2CO3 (2.00 g, 14.5 mmol) in DMSO (12 mL) was degassed with Ar before being charged with CuI (0.136 g, 0.716 mmol). The mixture in a sealed tube was heated at 130 C. overnight. After being cooled to room temperature, H2O and EtOAc were added. It was filtered through celite. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with MeOH in CH2Cl2 (0-5% MeOH) to give (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanol (0.39 g). |
Yield | Reaction Conditions | Operation in experiment |
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With triethylamine; In dichloromethane; at 0 - 20℃; for 4.0h; | a) 4-(tert-Butyldiphenylsilyloxymethyl)-1H-imidazole 4-Hydroxymethylimidazole hydrochloride ACROS (5 g, 37.1 mmol) was suspended in CH2Cl2 (100 ml) and TEA (12.87 ml, 92.8 mmol) was added. The solution was cooled at 0C and tert-butyldiphenylsilylchloride (15.3 ml, 55.7 mmol) was added. The reaction mixture was stirred for 30 min at 0C and at room temperature for 3.5 h. Water was added, the organic extract was washed with water and brine, then died over MgSO4. The solvent was removed under reduced pressure and the resulting oil was crystallized from diisopropylether to afford a white solid (8.17 g, m.p. = 135C). 1H-NMR (200 MHz, CDCl3) delta (ppm): 0.99 (s, 9H), 4.69 (s, 2H), 6.8 (s, 1H), 7.2-7.65 (m, 11 H). |
Yield | Reaction Conditions | Operation in experiment |
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With triethylamine; In acetonitrile; for 6.0h;Heating / reflux; | To a solution of ethyl 3-ethoxy-7-methyl-6-nitroquinoxaline-2-carboxylate (2.00 g, 6.55 mmol) in carbon tetrachloride (200 ml) was added N-bromosuccinimide (3.51 g, 19.7 mmol), then the reaction mixture was heated to 80 C. 2,2'-Azobisisobutyronitrile (215 mg, 1.31 mmol) was added to the reaction mixture and the mixture was refluxed for 6 hours. After cooling, the insolubles were filtered off and solvent was distilled off. After dissolved the residue obtained into acetonitrile (50 ml), <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (2.21 g, 16.4 mmol) and triethylamine (2.28 ml, 16.4 mmol) were added and the mixture was refluxed for 6 hours. The reaction mixture was distilled off under reduced pressure and the residue obtained was purified by means of silica gel column chromatography [ethyl acetate] to obtain 293 mg of the title compound as yellowish white powder. Yield 11%. 1H-NMR(CDCl3,delta):1.44(3H,t,J=7.3 Hz),1.50(3H,t,J=7.3 Hz), 4.51(2H,q,J=7.3 Hz),4.55(2H,s),4.63(2H,q,J=7.3 Hz),5.77(2H,s), 7.11(1H,s),7.41(1H,s),7.58(1H,s),8.63(1H,s). |
Yield | Reaction Conditions | Operation in experiment |
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8% | With triethylamine; In acetonitrile; at 120℃; for 24.0h; | REFERENTIAL EXAMPLE 4 5-Acetamido-2-((4-hydroxymethyl)imidazole-1-yl)-4-nitrobenzotrifluoride To a solution of 5-acetamido-2-fluoro-4-nitrobenzotrifluoride (2.00 g, 7.51 mmol) in acetonitrile (40 ml) were added (4-hydroxymethyl)imidazole hydrochloride (5.07 g, 37.6 mmol) and triethylamine (10 ml), and the mixture was stirred for 24 hours at 120 C. in sealed tube. After cooling, ethyl acetate was added to the reaction mixture and washed with brine. Then, this was dried over anhydrous sodium sulfate and solvent was distilled off. The residue obtained was submitted to silica gel column chromatography [methylene chloride-methanol (50:1 20:1)] to obtain 198 mg of the title compound as pale yellow powder. Yield 8%. 1H-NMR(DMSO-d6,delta):2.12(3H,s),4.41(2H,d,J=5.9 Hz), 5.02(1H,t,J=5.9 Hz),7.26(1H,s),7.79(1H,s), 8.13(1H,s),8.14(1H,s),10.69(1H,s). |
Yield | Reaction Conditions | Operation in experiment |
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23% | With potassium carbonate; In dimethyl sulfoxide; at 90℃; for 24.0h; | A mixture of 600 mg (4.36 mmol) of 4-hydroxymethylimidazol hydrochloride, 1.84 g (13.4 mmol) of anhydrous potassium carbonate, 40 mL of dimethylsulfoxide, and 1 g (3.61 mmol) of 3-(3,4-difluorophenyl)-5-(3-isoxazoylaminomethyl)isoxazole (Intermediate 7) was heated at 90C with stirring for 24 h under an inert atmosphere, allowed to cool, poured over 400 mL of a saturated sodium chloride solution, and extracted three times with 300 mL of ethyl acetate. The extracts were dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure and the obtained residue was chromatographed on a silica gel column with dichloromethane/methanol (20:1) as eluant. 300 mg (yield = 23 %) of a yellow solid were obtained. IR (KBr): 3300, 3100, 1595 cm-1. Mass spectrum (m/e): 355 (M+). 1H-NMR (200 MHz, CDCl3, ? ppm): 8.44 (s, 1H), 8.20-6.95 (m, 8H), 6.1 (s, 1H), 4.50 (d, 2H), 3.30 (s, 2H), 3.00 (br, 2H). |
Yield | Reaction Conditions | Operation in experiment |
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50% | With sodium carbonate; In 1,4-dioxane; water; at 20℃; for 24.0h;Heating / reflux; | A mixture of 1,2,3,4-tetrahydro-quinoline (Intermediate F1) (Commercially available from Aldrich) (1.62 mL, 12.6 mmol) and 4-hydroxymethyl-imidazole hydrochloride salt (commercially available from Aldrich) (Intermediate F2) (0.70 g, 5.1 mmol) and sodium carbonate (1.6 g, 15.1 mmol) in water (20 mL) and dioxane (10 mL) were heated at reflux for 24 h. The mixture was cooled to rt and extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and freed of solvent. The resultant oil was purified by chromatography on silica gel with 5% NH3-MeOH: dichloromethane to give 1-(1H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (Intermediate F3) as a solid, 0.54 g (50%). 1-(1H-Imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (Intermediate F3)was subjected to the appropriate process steps in Method A to produce 4-(3,4-dihydro-2H-quinolin-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 11). 1H NMR (300 MHz, DMSO-d6): delta12.0 (s, 1H), 11.8 (s, 1H), 6.93 (t, J=6.9 Hz, 1H), 6.87 (d, J=7.2 Hz, 1H), 6.66-6.63 (m, 1H), 6.63 (s, 1H), 6.50 (t, J=6.9 Hz, 1H), 4.18 (s, 2H), 3.28 (t, J=6.3 Hz, 2H), 2.67 (t, J=6.3 Hz, 2H), 1.90-1.84 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
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With sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; | REFERENCE EXAMPLE 106 To a mixture of 1H-imidazol-4-ylmethanol hydrochloride (4.55 g), imidazole (11.5 g) in N,N-dimethylformamide (46 ml) was added tert-butyldimethylsilyl chloride (15.3 g) at 0 C. After stirring for 14 hours at ambient temperature, the reaction mixture was poured into water (heat evolution) and extracted with ethyl acetate (200 ml*2). The combined organic extracts were washed with an aqueous saturated solution of sodium hydrogencarbonate (200 ml), water (200 ml*2) and brine (200 ml). The organic layer was dried over magnesium sulfate and filtered. After evaporation of the solvent, the residue was chromatographed on silica gel eluding with a mixture of dichloromethane-methanol (1%, 2% and then 4%) to give tert-butyl(dimethyl)silyl 1H-imidazol-4-ylmethyl ether (6.68 g) as colorless crystals. Mass: 213 (m/z, (M+H)+) NMR(DMSO-d6, delta): 0.03(6H,s), 0.85(9H, s), 4.53(2H,s), 6.87(1H, br s), 7.51(1H, br s), 11.88(1H, br s). |
Yield | Reaction Conditions | Operation in experiment |
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With triethylamine; In dichloromethane; N,N-dimethyl-formamide; | PREPARATION EXAMPLE 54 Synthesis of 4-(tert-Butyldimethylsilyloxymethyl)-imidazole 4-Hydroxymethylimidazole hydrochloride (5.03 g) was dissolved in a mixed solvent of dichloromethane (90 mL) and DMF (20 mL), and to the solution triethylamine (8.25 g) was added at 0 C. tert-Butyldimethylchlorosilane (6.14 g) was then added to the mixture, and the resultant mixture was stirred at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel (chloroform:methanol=20:1) to obtain the title compound. Yield: 6.21 g (79%). 1H-NMR (400 MHz, CDCl3) delta: 0.08 (s, 6H), 0.91 (s, 9H), 4.73 (s, 2H), 6. 94 (s, 1H), 7.59 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
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47% | With triethylamine; In acetonitrile; | EXAMPLE 1 Ethyl 2-ethoxy-6-(4-(hydroxymethyl)imidazole-1-yl)-7-nitroquinoline-3-carboxylate To a solution of ethyl 2-ethoxy-6-fluoro-7-nitroquinoline-3-carboxylate (1.00 g, 3.24 mmol) in acetonitrile (10 ml) were added <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (2.18 g, 16.2 mmol) and successively triethylamine (3 ml), and the mixture was stirred for 16 hours at 120 C. in a sealed tube under shading. After cooling, solvent was distilled off and the residue was submitted to silica gel column chromatography [dichloromethane-methanol(50:1?20:1)] under shading to obtain 583 mg of title compound as light brown powder. Yield 47%. 1H-NMR(DMSO-d6, delta): 1.35(3H,t,J=7.3 Hz), 1.42(3H,t,J=7.3 Hz), 4.38 (2H,q,J=7.3 Hz), 4.42(2H,d,J=6.8 Hz), 4.58(2H,d,J=7.3 Hz), 5.05(1H, t,J=5.4 Hz), 7.27(1H,s), 7.88(1H,s), 8.39(1H,s), 8.50(1H,s), 8.87 (1H,s). |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate; In water; ethyl acetate; N,N-dimethyl-formamide; | (a) [1-(4-Chlorobenzyl)-1H-imidazol-4-yl]methanol 4-Chlorobenzylchloride (1.2 g) was dissolved in N,N-dimethylformamide (20 ml), 4(5)-hydroxymethylimidazole hydrochloride (1.0 g) and potassium carbonate (4 g) were added and the mixture heated at 90 C. for 20 hours. Water and ethyl acetate were added, the organic phase was separated, washed with brine, dried and the solvent removed by evaporation. The residue was purified by chromatography (dichloromethane:methanol, 9:1) to give the product as a mixture of regioisomers (0.5 g). This material was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
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76% | With triethylamine; In tetrahydrofuran; ethyl acetate; | Referential Example 8 4-(Dichloromethyl)-2-(4-(hydroxymethyl)imidazole-1-yl)-5-nitro-benzotrifluoride To a solution of the compound of Referential example 7 (5.31 g, 18.2 mmol) in tetrahydrofuran (40 ml) were added <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (4.90 g, 36.4 mmol) and triethylamine (7.37 g, 72.8 mmol), and the mixture was refluxed for 1.5 hours. After cooling, ethyl acetate was added to the reaction mixture, washed with brine, then dried over anhydrous magnesium sulfate and solvent was distilled off. The residue obtained was submitted to silica gel column chromatography [ethyl acetate-hexane(3:1)?ethyl acetate] to obtain 5.15 g of title compound as pale yellow powder. Yield 76%. 1H-NMR(DMSO-d6, delta): 4.44(2H,d,J=4.4 Hz), 5.09(1H,t,J=4.4 Hz), 7.39 (1H,s), 7.78(1H,s), 7.92(1H,s), 8.19(1H,s), 8.59(1H,s). |
Yield | Reaction Conditions | Operation in experiment |
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In methanol; aqueous HBr; ethanol; chloroform; water; isopropyl alcohol; | EXAMPLE 104 2-{2-[(1H-Imidazol-4-yl)methylthio]ethylamino}-5-nitropyridine 3 g (22 mmol) of <strong>[32673-41-9]4-hydroxymethyl-1H-imidazole hydrochloride</strong> and one molar equivalent of 2-aminoethanethiol (2.2 g) in 45 ml of aqueous HBr (48%) are brought to reflux for 18 h. The dark-red solution is then evaporated to dryness and the 4-[(2-aminoethyl)thiomethyl]-1H-imidazole dihydrobromide solid residue is washed with 30 ml of an absolute ethanol/ether (1/1) mixture (yield=95%), M.p.: 178-179 C. A solution of 5 g (15mmol) of 4-[(2-aminoethyl)thiomethyl]-1H-imidazole dihydrobromide in 5 ml of water is basified to a pH of 11 with 4.3 g (31 mmol) of K2 CO3 in 15 ml of water. Extraction with 2-propanol provides the amine base which is freed of the inorganic material by subsequent washing with 2-propanol. 2 g (12.7 mmol) of the amine and 2 g (12.7 mmol) of 2-chloro-5-nitropyridine in 20 ml of 2-propanol are brought to reflux for 18 h. On leaving to stand, an orange solid settles and the latter is collected and chromatographed on a column of silica gel which is eluted with a mixture of chloroform and methanol (1, 5, 10 and 20%). The combined fractions are concentrated under reduced pressure to dryness and the resulting solid is purified by preparative reverse-phase high performance liquid chromatography. The product is crystallized from absolute ethanol to give pale-yellow crystals, M.p.: 145-147 C. |
Yield | Reaction Conditions | Operation in experiment |
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In N,N-dimethyl-formamide; | Step F Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong> (35.0 g, 260 mmol) in dry DMF (250 ml) at ambient temperature was added Et3 N (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in of DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title compound as a white solid which was sufficiently pure for use in the next step. |
Yield | Reaction Conditions | Operation in experiment |
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With sodium carbonate; In N,N-dimethyl-formamide; at 70℃; | To a solution of 1-fluoro-2-nitro-4- (trifluoromethyl)benzene (1.04 mL, 7.43 mmol) and (IH- pyrrol-3-yl)methanol hydrochloride salt (1.0 g, 7.43 mmol) in DMF (10 mL) was added Na2CO3 (2.36 g, 22.3 mmol) . The resulting mixture was heated at 7O0C overnight. The mixture was cooled to room temperature and concentrated under reduced pressure. The mixture was reconstituted in EtOAc (50 mL) and washed with 9% aq. Na2CO3 (10 mL) , brine (10 mL) , dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford (1- (2-nitro-4- (trifluoromethyl)phenyl) -IH-imidazol-4-yl)methanol . |
Yield | Reaction Conditions | Operation in experiment |
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39% | With thionyl chloride; In N,N-dimethyl-formamide; | To 0.5 g (3.7 millimoles) of <strong>[32673-41-9]4-hydroxymethylimidazole hydrochloride</strong> was added 3 ml of thionyl chloride and reaction was carried out at 50 C. for 2 hours. The excess of thionyl chloride was removed by distillation under reduced pressure. The residue was dissolved in 10 ml of DMF and a solution of 1.1 g (6.3 millimoles) of 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline in 5 ml of DMF was added to the above solution at 100 C. Reaction was carried out for 1 hour. DMF was removed from the reaction mixture by distillation under reduced pressure. An aqueous solution of sodium hydrogen-carbonate was added to the residue and the mixture was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain a light-green oil. The oil was purified by the silica gel column chromatography (developing solvent; ethyl acetate) to obtain 0.35 g (the yield was 39%) of 4-[1-(2,2,4-trimethyl-1,2,3,4-tetrahydroquinolyl)methyl]imidazole in the form of a colorless crystal. |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride; sodium hydroxide; PPA; In methanol; 4-Methylphenethyl alcohol; water; acetonitrile; | C. By hydrolysis of the esters obtained by the Friedel-Crafts reaction. 2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoic acid and 2-hydroxy-5-[(1H-imidazol-4-yl)methyl]-benzoic acid (hydrochloride). 181 g (1.35 mole) of 1H-imidazole-4-methanol hydrochloride are added in portions to a mixture of 156 ml (1.2 mole) of methyl 2-hydroxybenzoate and 675 g of polyphosphoric acid heated to 80 C. The reaction mixture is maintained with good stirring at this temperature for 288 hours. The mixture is then decomposed on ice, and extracted twice with toluene. The aqueous phase is alkalinized to pH 9.5 by the addition of 790 ml of a saturated aqueous solution of sodium hydroxide. The mineral salts which precipitate are removed by filtration and washed with methanol. The methanolic washing solution is added to the aqueous phase and the resulting mixture is concentrated with partial elimination of the methanol. The solution is then alkalinized to pH 10.3 by addition of a 10N aqueous solution of sodium hydroxide, and is heated at 100 C. for one hour and a half so as to saponify the esters. The aqueous solution is neutralized to pH 7.5 by addition of 10 N hydrochloric acid, filtered on Norit (activated carbon) and the filtrate is evaporated under reduced pressure. The residue is taken up three times in succession in a toluene-ethanol mixture and dried by azeotropic distillation. It is then partially dissolved in hot methanol and the insoluble mineral salts are removed by filtration. The filtrate is evaporated under reduced pressure, the residue is redissolved in a minimum of water, and purification is then carried out by passing through a column of Amberlite IR93 (height of the column: 60 cm; diameter: 8 cm; equivalence: 2.64 mole). Excess 1H-imidazole-4-methanol, together with its polymers, are eluted with water (the pH of the elude varies from 11.2 to 7.3). The elution is then continued with a 4% aqueous solution of hydrochloric acid. The acid elude (9 liters) is adjusted to pH 7.7 by addition of a saturated agueous solution of sodium hydroxide and is then evaporated under reduced pressure. The residue thus obtained is once again dried by azeotropic distillation with a toluene-ethanol mixture, and is then taken up in 1.6 liter of acetonitrile. It is then filtered. The residue on the filter (129 g) is chromatographed on silica (800 g, 15 mum) after having been previously deposited on 300 g of silica (0.2 to 0.5 mm) (eluent: 75:25 v/v ethyl acetate-ethanol). 5.99 g of 2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoic acid is thus obtained. M.P.: 245-252 C. (water). At the same time, 31 g of 2-hydroxy-5-[(1H-imidazol-4-yl)methyl]-benzoic acid are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.8% | In sulfuric acid; | 1. Methyl 5-tert-butyl-2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate hydrochloride. 50 g of 1H-imidazole-4-methanol hydrochloride are reacted with 60 g of methyl 5-tert-butyl-2-hydroxybenzoate in 150 ml of concentrated sulfuric acid at 20 C. for 21 hours. The reaction mixture is then cautiously decomposed on ice. The solid product is filtered off, purified by chromatography and then converted into its hydrochloride. 1.1 g of methyl 5-tert-butyl-2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate hydrochloride is obtained. Yield: 2.8%. M.P.: 185-186 C. NMR (DMSO): delta 1.3(9H,s), 3.45(3H,s), 4.1(2H,s), 7.3(1H,s), 7.75(2H,m), 9.0(1H,s), 10.5 to 13,0 (3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.2% | With formic acid; | 4. Ethyl 6-hydroxy-3-[(1H-imidazol-4-yl)methyl]-2-methylbenzoate and ethyl 2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-6-methylbenzoate. These two compounds are simultaneously prepared from a mixture of 80.8 g (0.448 mole) of <strong>[6555-40-4]ethyl 2-hydroxy-6-methylbenzoate</strong>, 225 ml of formic acid and 51.5 g (0.382 mole) of 1H-imidazole-4-methanol hydrochloride, heated at reflux temperature for 53 hours. The products obtained are separated and purified by chromatography on silica gel (eluent: 94:6:0.5 v/v/v dichloromethane-methanol-ammonia). 7.2 g of ethyl 6-hydroxy-3-[(1H-imidazol-4-yl)methyl]-2-methylbenzoate are obtained. Yield: 7.2%. M.P.: 42-45 C. NMR (CDCl3): delta 1.36(3H,t), 2.34(3H,s), 3.83(2H,s), 4.37(2H,q), 6.52(1H,s), 6.70(1H,d), 7.08(1H,d), 7.45(1H,s), 10.0(2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In sulfuric acid; | 5.a. methyl 5-bromo-2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-4-methylbenzoate. 95.6 g (0.71 mole) of 1H-imidazole-4-methanol hydrochloride are added in portions, at ambient temperature, to a solution of 87 g (0.355 mole) of <strong>[39503-57-6]methyl 5-bromo-2-hydroxy-4-methylbenzoate</strong> (T. M. CRESP et al., J. Chem. Soc. Perkin I, (1973), 340) in 900 ml of concentrated sulfuric acid. Stirring is maintained for 234 hours. The reaction mixture is then poured cautiously on ice and the aqueous phase is neutralized to pH 8 by the addition of a saturated aqueous solution of sodium hydroxide. There is extracted with ethyl acetate. The organic layer is evaporated under reduced pressure and the residue is purified by chromatography on 1.4 kg of silica (eluent: 9:1 v/v dichloromethane-methanol). The product obtained is chromatographed a second time on 400 g of silica (eluent: 95:5:0.5 v/v/v dichloromethane-methanol-ammonia). 2.4 g of methyl 5-bromo-2-hydroxy-3-[(1H-imidazol-4-yl)methyl] -4-methylbenzoate are obtained, which are sufficiently pure to be used as such in the following step. NMR (DMSO): delta 2.43(3H,s), 3.90(3H,s), 3.96(2H,s), 6.62(1H,s), 7.51(1H,s), 7.87(1H,s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With sodium hydroxide; formic acid; In water; | 2. Methyl 2,6-dihydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate. 95.84 g (0.57 mole) of <strong>[2150-45-0]methyl 2,6-dihydroxybenzoate</strong>, 190 ml of formic acid and 51.14 g (0.38 mole) of 1H-imidazole-4-methanol hydrochloride are mixed together. The mixture is heated at reflux temperature and the formic acid-water azeotropic mixture is distilled for 15 minutes. Then, the reflux temperature is maintained for 17 hours. The reaction mixture is poured in water. Excess <strong>[2150-45-0]methyl 2,6-dihydroxybenzoate</strong> is extracted with toluene, and the aqueous phase is then neutralized to pH 7-8 by the addition of a saturated aqueous solution of sodium hydroxide. It is then extracted with dichloromethane, the organic phases are dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica gel (eluent: 94:6:0.6 v/v/v dichloromethane-methanol-ammonia). 14.8 g of methyl 2,6-dihydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoate are obtained; the product is contaminated by traces of residual solvents. Yield: 13%. NMR (DMSO): delta 3.72(2H,s), 3.81(3H,s), 6.33(1H,d), 6.86(1H,s), 7.06(1H,d), 7.73(1H,s), 9,5 to 10.2(3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium chloride; In N-methyl-acetamide; | A. To a flask containing 4 gms 4-hydroxymethyl imidazole hydrochloride in 30 ml dimethylformamide add 3.1 ml vinylethyl ether and 50 mg paratoluene sulfonic acid. Stir for 11/2 hours until the reaction is complete. Extract from saturated K2 CO3 /NaCl with ethylacetate to obtain 1-ethoxy-1-(imidazol-4-yl)methoxy ethane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dibromo sulfoxide; | 0.2 Mol 4-hydroxymethyl imidazole hydrochloride is added to 270 ml thionyl bromide, which has been cooled to 0C. The yellow-coloured solution is allowed to return to room temperature. Excess thionyl bromide is distillated for 45 minutes under reduced pressure. The remainder solidifies upon cooling. The yield of 4-bromomethyl imidazole hydrobromide salt is about 50%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Bis(4-Chlorophenyl)borinic acid 4-(hydroxymethyl)imidazole ester (126) In a similar manner as in Example 121, the titled compound was obtained from the reaction of bis(4-chlorophenyl)borinic acid with <strong>[32673-41-9]4-(hydroxymethyl)imidazole hydrochloride</strong>. The product was obtained as white crystals. (ES-)(m/z) 328.79, MF C16H13BCl2N2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1H-Imidazole-4-methanol hydrochloride (5.0 g, 37.2 mmol) in dimethylformamide (100 mL) was added dropwise over 30 minutes to a suspension of sodium hydride (60% dispersion in mineral oil, 2.97 g, 74.3 mmol) in dimethylformamide (200 mL) and the mixture was stirred at room temperature for 2 hours. The mixture was cooled to 0 C. and a solution of [2-(chloromethoxy)ethyl]trimethysilane (6.59 mL, 37.2 mmol) in tetrahydrofuran (50 mL) was added dropwise over 15 minutes. The mixture was stirred at room temperature overnight, then water (100 mL) was added and the solvent was evaporated under reduced pressure. Toluene (200 mL) was added and evaporated under reduced pressure. Water (100 mL) was added and the mixture was extracted with ethyl acetate (3×150 mL). The combined organic fractions were washed with water (100 mL) and brine (150 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH (95:5 increasing to 90:10), to give the title compound as a mixture of isomers (4.82 g, 57%). 1H NMR (400 MHz, CDCl3) delta Major isomer, delta 0.00 (9H, s), 0.84-0.96 (2H, m), 3.43-3.56 (2H, m), 4.62 (2H, s), 5.24 (2H, s), 6.99 (1H, s), and 7.56 (1H, s); Minor isomer, delta 0.00 (9H, s), 0.84-0.96 (2H, m), 3.43-3.56 (2H, m), 4.67 (2H, s), 5.36 (2H, s), 7.05 (1H, s), and 7.56 (1E, s). m/z (ES+) 229 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20℃; | To a slurry of <strong>[32673-41-9]4-hydroxymethylimidazole hydrochloride</strong> (1.35 g, 10.0 mmol) and TEA (2.09 mL, 15 mmol) in DMF (5 mL) at 0 C. was added a solution of di-tert-butyl dicarbonate (2.18 g, 10.0 mmol) in THF (15 mL), dropwise over 5 min. The cooling bath was removed, the mixture was stirred at rt overnight and concentrated in vacuo. The residue was partitioned between EtOAc/H2O and the layers were separated. The organic layer was washed (2×H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo affording 1.14 g colorless oil which was determined (LC/MS) to be a 3:1 mixture of the title compounds, which was used without further purification: Major regioisomer: MS (ES) m/z 199 (M+H, 9%), 221 (M+Na, 13%), 143 (100%). Minor regioisomer: MS (ES) m/z 199 (M+H, 15%), 113 (100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.5% | With hydrogenchloride; ammonium cerium (IV) nitrate; sodium ethanolate; In ethanol; acetonitrile; at 60℃; for 8.0h;pH 10.0; | A mixture of acetonitrile and ethanol in a volume ratio of 2: 1 was added to the reactor,100 mmol of 1,3-dihydroxyacetone and 200 mmol of formaldehyde were dissolved in an organic solvent,100 mmol of cerium ammonium nitrate was added,Under normal pressure 60 conditions,Adding sodium ethoxide to adjust the pH to 10,15 mmol of catalyst was added,Stirring reaction 8h, obtained 4-hydroxymethyl imidazole,After completion of the reaction,Dropping concentrated HCl,Adjust pH = 2,filter,The filtered solid,Washed with saturated brine,Recrystallization from ethanol,Dried in vacuo to give the product 4-hydroxymethylimidazole hydrochloride.The purity of the prepared 4-hydroxymethylimidazolidine hydrochloride was 98.2%The yield was 87.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate; In acetonitrile; at 70℃; | 4-imidazolemethanolhydrochloride (1.34 g, 10 mmol), 4-tertbutylbenzyl chloride (1.82 g, 10 mmol) and K2CO3 (4.14 g,30 mmol) were heated at 70C in acetonitrile (CH3CN) overnight.The reaction mixture was filtered and the filtrate wasconcentrated under reduced pressure to give a crude residue.Purification by column chromatography on silica gel (15:1 v/vCH2Cl2:MeOH) afforded the intermediates compound,which reacted with 4-tert-butyl benzyl chloride (1.82 g,10 mmol) again at 70C in CH3CN for 3 d to generate thetitle compound NHC as a white solid (83% yield). ESI-MS(m/z): 391 [M-Cl-]+ |
Tags: 32673-41-9 synthesis path| 32673-41-9 SDS| 32673-41-9 COA| 32673-41-9 purity| 32673-41-9 application| 32673-41-9 NMR| 32673-41-9 COA| 32673-41-9 structure
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