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CAS No. : | 7467-35-8 |
Formula : | C9H10N2O |
M.W : | 162.19 |
SMILES Code : | OCC1=NC2=CC=CC=C2N1C |
MDL No. : | MFCD00464051 |
InChI Key : | SQRSIOZFPSFABI-UHFFFAOYSA-N |
Pubchem ID : | 344177 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
50.4% | 2- hydroxymethyl-l -methyl-1 H-benzimidazole (Compound 49a)A suspension of l -methyl-2-formyl-l H-benzimidazole (500 mg, 3.12 mmol) and NaBH4 (134 mg, 3.43 mmol) in anhydrous THF (25 ml) was stirred for 24 hours at r.t.. The reaction mixture was quenched with water, extracted with EtOAc, dried over Na2S04 and evaporated to dryness in vacuo. The crude was purified by automated flash chromatography (HorizonTM - Biotage) eluting with CHC13 - 1.7M NH3 sol. in MeOH 100:2 giving the title product as white solid. Yield: 50.4 %. MS: [ +H]+ = 163.5 | |
Example 12; (1-Methyl-1H-benzoimidazol-2-yl)-methanol; Sodium borohydride (472 mg, 12.48 mmol) was added to the solution of 1-methyl-1H-benzoimidazole-2-carbaldehyde (1 g, 6.24 mmol) in ethanol (50 mL). The reaction mixture was stirred at room temperature for overnight. The reaction mixture was condensed, the residue was diluted with ethyl acetate; water was added. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and condensed to give off-white solid as product (953 mg, 94%). This product was used in the later steps without further purification.1HNMR (300 MHz, CDCl3): (ppm) 7.63 (m, 1H), 7.21 (m, 3H), 4.84 (s, 2H), 3.75 (s, 3H) | ||
With methanol; sodium tetrahydridoborate; at 0 - 20℃; for 5h; | To a 0C solution of 1 -methyl- lH-benzimidazole-2-carbaldehyde (1.1 g, 6.8 mmol) in anhydrous methanol (50 mL) was added sodium borohydride (350 mg, 9.3 mmol). The reaction mixture was stirred at room temperature for 5 hours. Saturated ammonium chloride solution (20 mL) was added. Methanol was evaporated. The resultant mixture was extracted with EtOAc (3 x 50 mL) and CH2Cl2 (1 x 50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. (1 -methyl- lH-benzimidazol-2-yl)methanol was obtained (1.1 g, 99% yield). The product was used without further purification. |
With sodium tetrahydridoborate; In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; | To a solution of 1-methyl- 1H-benzo[d]imidazole-2-carbaldehyde (5-5a, 150 mg, 936.49 umol, 1 eq) in THF (3 mL) was added NaBH4 (38.97 mg, 1.03 mmol, 1.1 eq) at 20C under N2. The mixture was stirred at 20C for 1 hour. LCMS showed 5-5a was comsumed completely and desired mass was detected. The reaction mixture was quenched by addition water (30 mL) at 20C. The aqueous phase was extracted with ethyl acetate (25 mL*2). The combined organic phase was washed with brine (20 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-TLC (ethyl acetate: methanol = 20:1) to give 5-5b as a white solid.1H NMR (400MHz, CDCl3-d) 7.77-7.67 (m, 1H), 7.34-7.28 (m, 2H), 7.27- 7.23 (m, 1H), 4.91 (s, 2H), 3.83 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With Dess-Martin periodane; In dichloromethane; at 4℃; for 1h; | General procedure: Dess-Martin reagent (1.1 mmol) was added to a solution of benzimidazol-2-ylmethanol 4 or 7(1 mmol) in methylene chloride (10 mL). The reaction mixture was stirred at 4 C for 1 h prior tobeing quenched with saturated aqueous sodium thiosulfate solution (3 mL). The subsequent mixturewas extracted with methylene chloride (3 × 10 mL). The combined organic extracts were dried overanhydrous magnesium sulfate and concentrated in vacuo to provide a crude product, which wascrystallized from methanol to give corresponding product.1-Methyl-1H-benzimidazole-2-carboxaldehyde (1) [3] was obtained as beige solid in 30%yield. M.p. 134-136C from methanol. 1H NMR (500 MHz, CDCl3) δ 4.12 (s, NMe), 7.35-7.39 (m,1Harom.), 7.43-7.48 (m, 2Harom.), 7.90 (d, 1Harom., J = 10.3 Hz), 10.09 (s, 1H, CHO). 13C NMR (125MHz, CDCl3) δ 31.2, 110.5, 122.3, 124.0, 126.8, 136.9, 142.7, 146.1, 185.0. |
With manganese(IV) oxide; In ethyl acetate; at 65℃; for 1h; | General procedure: A solution of 2a-2d (2 mmol), MnO2 (3.48 g, 40 mmol) was added to EtOAc (120 mL), then refluxedat 65 C for 1 h (monitored by TLC). Afterwards the solution was filtered, and concentrated in vacuoto give pure compounds 3a-3d (in 60%-76% yield) [17]. |
Tags: 7467-35-8 synthesis path| 7467-35-8 SDS| 7467-35-8 COA| 7467-35-8 purity| 7467-35-8 application| 7467-35-8 NMR| 7467-35-8 COA| 7467-35-8 structure
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