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Chemical Structure| 152628-00-7

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Product Details of [ 152628-00-7 ]

CAS No. :152628-00-7
Formula : C13H16N2O2
M.W : 232.28
SMILES Code : CCCC1=NC2=CC(=CC(C)=C2N1)C(=O)OC
MDL No. :MFCD03844703

Safety of [ 152628-00-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 152628-00-7 ]

* 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.

  • Downstream synthetic route of [ 152628-00-7 ]

[ 152628-00-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 152628-00-7 ]
  • [ 152628-03-0 ]
YieldReaction ConditionsOperation in experiment
80% With water; sodium hydroxide; In methanol; at 80℃;Product distribution / selectivity; Example 1:Methyl-4-methyl-2-propyl-lH-benzimidazole-6-carboxylate (40 gms, 0.172 moles) was suspended in methanol (200 ml) and stirred for few minutes. Sodium hydroxide (13.76 gms, 0.344 moles) dissolved in water (50 ml) was added to the reaction mass and the temperature is maintained at 80C. After completion of the reaction, methanol was evaporated under reduced pressure and water (100 ml) was added to the crude mass at 5-10 C. Then adjusted the pH of the crude mass to 6- 6.5 and the obtained solid was filtered. The solid was washed with water and dried at temperature of 45-50 C under vacuum (700 mm) to yield 2-n-propyl-4-methyl- 6-carboxy benzimidazole (30gms, Yield: 80 %).
Reference Example A3: 4-Methyl-6-(2-oxazolyl)-2-propylbenzimidazole [step 1] 6-Methoxycarbonyl-4-methyl-2-propylbenzimidazole (EP502314; 500 mg, 2.29 mmol) was suspended in ethanol (15 mL), 4 mol/L aqueous sodium hydroxide solution (3.1 mL) was added, and the mixture was stirred under reflux for 7 hr. The mixture was concentrated under reduced pressure, and water (20 mL) was added. Under ice-cooling, the mixture was adjusted to pH 1 with 2 mol/L hydrochloric acid, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in dichloromethane, aminoacetaldehyde dimethylacetal (0.50 mL, 4.58 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (527 mg, 2.75 mmol) and 1-hydroxybenzotriazole (421 mg, 2.75 mmol) were added, and the mixture was stirred at room temperature for 6 hr. To the mixture were added saturated aqueous sodium hydrogen carbonate solution (100 mL) and chloroform (100 mL), and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 6-(2,2-dimethoxyethylcarbamoyl)-4-methyl-2-propylbenzimidazole. ESI-MS m/z; 306 (M + H)+; 1H-NMR (CDCl3, delta): 1.02 (t, J = 7.3 Hz, 3H), 1.82-1.97 (m, 2H), 2.65 (s, 3H), 2.92 (t, J= 7.3 Hz, 2H), 3.45 (s, 6H), 3.64 (t, J = 5.3 Hz, 2H), 4.52 (t, J = 5.3 Hz, 1H), 6.42 (s, 1H), 7.89 (s, 1H).
With sodium hydroxide; In methanol; water; for 2h;Reflux; General procedure: A solution of an appropriate ester (25.01mmol) in methanol (25mL) was added to a solution of NaOH (2.0g) in water (25mL), and the mixture was heated under reflux for 2h. After evaporation of methanol, the pH was adjusted to 4-5 by addition of aqueous citric acid. The precipitated solid was filtered, washed with ethanol and dried to yield carboxylic acid. The resulting compound was dissolved in polyphosphoric acid (10mL) at 150C. N-Methyl-o-phenylenediamine dihydrochloride (3.65g, 18.8mmol) was added to the mixture for 4 times in 4h. After stirring at 150C for 10h, the mixture was cooled and then poured into ice water (30mL). The pH was adjusted to 10 by addition of concentrated ammonia (ice cooling). The precipitated solid was filtered off, dried, and boiled in ethyl acetate (300mL). After cooling, the precipitated solid was filtered off, washed with diethyl ether, and dried to give the product as white solid.
  • 2
  • [ 67-56-1 ]
  • [ 152628-03-0 ]
  • [ 152628-00-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; for 12h;Heating / reflux;Product distribution / selectivity; Preparation 1 7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic Acid Methyl Ester 7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (30.0 g, 137 mmol) was dissolved in MeOH (550 mL) and added to a round bottom flask, followed by the addition of 20 mL of a hydrogen chloride solution (30:70, conc. HCl:water). The mixture was refluxed for 12 hours then concentrated under reduced pressure to afford the title compound as a yellow solid (31.8 g, 137 mmol). MS m/z: [M+H+] calcd for C13H16N2O2, 233.12; found 233.2.
With sulfuric acid; for 36h;Heating / reflux;Product distribution / selectivity; 7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid methyl ester (7a): Sulfuric acid (12 mL, 0.22 mol) was added to <strong>[152628-03-0]7-methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid</strong> (30 g, 136 mmol) dissolved in MeOH (670 mL, 16 mol). The mixture was refluxed for 36 hours and concentrated in vacuo. The recovered material was dissolved in 500 mL EtOAc and washed with a saturated NaHCO3 solution. The organic layer was dried over MgSO4 and concentrated to provide Intermediate (7a) as a brown solid (29.1 g). MS m/z: [M+H+] calcd for C13H16N2O2, 233.1; found 233.2.
With hydrogenchloride; In water; at 70℃; for 27h;Heating / reflux; Example 6 Preparation of methyl 7-methyl-2-propyl-3H-benzo[d]imidazole-5-carboxylate (compound 11):5 g (23 mmol) 7-methyl-2-rhoropyl-3H-benzo[d]imidazole-5-carboxylic acid was added to 100 ml methanol, stirred and 3 ml concentrated hydrochloric acid (37%) was added and heated to 70 0C for 20 h. Another 3 ml concentrated hydrochloric acid was added and heated to reflux for 4 h. 4 ml concentrated hydrochloric acid was added and heated to reflux for 3 h. The solvent was removed under vacuum to give 6.6 g of crude compound 11.
 

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