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CAS No. : | 38993-84-9 | MDL No. : | MFCD02179522 |
Formula : | C5H8N2O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | PXGQMYCEAWZJJF-UHFFFAOYSA-N |
M.W : | 112.13 | Pubchem ID : | 2773450 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
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 |
---|---|---|
80% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 0.333333h; | 3-Methyl-3H-imidazole-4- carbaldehyde (10) (4.0 g, 15 mmol) was suspended in THF (10 mL), and the resulting solution cooled to 0°C. Lithium aluminum hydride (300 mg, 32.0 mmol) was added portion wise over 10 minutes, and the resulting suspension stirred for a further 10 minutes. Excess hydride was quenched by the addition of solid Na2SO4-IOH2O (~1 g) in large portions with vigorous stirring. Additional THF was added as needed to prevent solidification of the resulting slurry. The resulting suspension was stirred for a further hour, and then filtered to remove the sulfate salts, and the solvent was removed under reduced pressure to provide the title alcohol (1.3 g, 80percent). 1H NMR (400 MHz, ^-MeOH): delta 7.57 (s, IH), 6.89 (s, IH), 4.58 (s, 2H), 372 (s, 3H). 13C NMR (100 MHz, ^-MeOH): delta 140.1, 132.7, 128.1, 31.9, 31.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In dichloromethane; | (1 -Methyl- 1 H-imidazol-5-yl)methanol was converted to the corresponding alkyl chloride by reaction with thionyl chloride in DCM. N-[1 -(Fluoromethyl)cyclopropyl]-3- [(1 -methylpyrazol-4-yl)methyl]-2,4-dioxo-1 1H-quinazoline-6-sulfonamide (100 mg, 0.260 mmol), the alkyl chloride (37 mg, 0.286 mmol) and potassium carbonate (43 mg, 0.312 mmol) in DMF was conventionally heated to 70 °C for 4 h. Usual work-up afforded the desired product (37 mg, 0.074 mmol, 28percent) as an off-white powder. | |
With thionyl chloride;N,N-dimethyl-formamide; at 20℃; for 2h;Sonographic reaction; | Thionyl chloride (3.88mL, 53.5mmol) was added dropwise to 3-methyl-3H-imidazol-4- yl)-methanol (o.3g, 2.68mmol). The reaction was sonicated briefly, treated with DMF (1 drop) and allowed to stir at ambident temperature for 1 h. The volatiles were removed and the residue treated with diethyl ether. The diethyl ether was decanted and the procedure repeated 3 times. The semi-solid residue was treated with dimethylamine in THF (6.69mL, 13.38mmol) followed DMF (1 mL). The reaction was heated in a CEM microwave reactor at 8O0C for 30 minutes, treated with acetic acid (1 ml_) and purified by SCX cartridge to give the title compound (0.18g, 1.22mmol). LC-MS (method 1): R, 2.9 min, m/z 140 [MH]+. | |
With thionyl chloride;N,N-dimethyl-formamide; for 0.5h; | DMF (1 drop) was added to a slowly stirred solution of (3-methyl-3H-imidazol-4-yl)-methanol (11) (1.8 g, 16 mmol) dissolved in thionyl chloride (12 mL). After 30 minutes the solvent was removed under reduced pressure, and the resulting solid triturated with diethyl ether (20 mL). The resulting semi-solid was dried over night under vacuum, and used without further purification. 1H NMR (400 MHz, CI4-MQOR): delta 8.98 (s, IH), 7.63 (s, IH), 4.85 (s, 2H), 3.90 (s, 3H). 13C NMR (100 MHz, d4- MeOH): delta 138.3, 132.6, 120.5, 34.5, 33.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; formaldehyd; In water; | EXAMPLE 8 Preparation of 1-methyl-5-hydroxymethylimidazole To a suspension of 1.4 g (0.01 mol) of 1-methyl-5-carbmethoxyimidazole in 5 ml of water is added 0.8 g (0.02 mol) of sodium hydroxide, and the mixture was heated to reflux for 2 hours. To the mixture is added 4 ml of ~37percent aqueous formaldehyde solution, and the resultant mixture is heated at 80-90 for 2 hours. After completion of the reaction, the solvent is stripped off and the residue is extracted with ethyl acetate. The ethyl acetate extract was concentrated to give 1-methyl-5-hydroxymethylimidazole as a solid, m.p. 112°-114° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With manganese dioxide; In 1,4-dioxane; | EXAMPLE 32C 1-methyl-1H-imidazole-5-carbaldehyde A solution of Example 32B (2.3 g, 20 mmol) in dioxane (100 mL), was treated with manganese dioxide (17.3 g, 200 mmol), heated to reflux for 16 hours, cooled to room temperature, filtered through a pad of diatomaceous earth (Celite.(R).), and concentrated to provide the desired product of sufficient purity for subsequent use without further purification. 1H NMR (300 MHz, CDCl3) delta 9.77 (d, 1H), 7.79 (s, 1H), 7.62 (s, 1H), 3.95 (d, 3H). |
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