Alternatived Products of [ 49836-24-0 ]
Product Details of [ 49836-24-0 ]
CAS No. : | 49836-24-0 |
MDL No. : | |
Formula : |
C9H14O4
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
186.21
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 49836-24-0 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 49836-24-0 ]
* 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.
- Upstream synthesis route of [ 49836-24-0 ]
- Downstream synthetic route of [ 49836-24-0 ]
- 1
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[ 49836-24-0 ]
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[ 85290-78-4 ]
- 2
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[ 49836-24-0 ]
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[ 60-34-4 ]
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[ 85290-77-3 ]
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[ 85290-76-2 ]
- 3
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[ 5676-60-8 ]
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[ 49836-24-0 ]
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2-[1-(2-Methyl-benzooxazol-6-ylamino)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester
[ No CAS ]
- 4
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[ 49836-24-0 ]
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[ 177492-52-3 ]
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2-[1-(Benzooxazol-6-ylamino)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester
[ No CAS ]
- 5
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[ 10394-38-4 ]
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[ 49836-24-0 ]
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2-[1-(1-Methyl-1H-benzoimidazol-5-ylamino)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester
[ No CAS ]
- 6
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[ 49836-24-0 ]
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[ 5456-63-3 ]
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Ethyl 2-[N-(2-hydroxycyclohexyl)aminomethylene]-3-oxobutanoate
[ No CAS ]
- 7
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[ 49836-24-0 ]
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[ 31728-75-3 ]
- 8
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[ 49836-24-0 ]
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[ 85290-77-3 ]
- 9
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[ 49836-24-0 ]
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[ 85290-76-2 ]
- 10
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[ 49836-24-0 ]
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[ 89570-82-1 ]
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[ 148837-76-7 ]
Yield | Reaction Conditions | Operation in experiment |
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With sodium hydrogencarbonate; In ethanol; dichloromethane; water; |
Step C Synthesis of 1-(3-chloro-5-trifluoromethyl-2-pyridyl)-4-ethoxycarbonyl-1H-5-methylpyrazole To a solution of 30 g (0.14 mole) of 3-chloro-5-trifluoromethylpyrid-2-ylhydrazine in 500 mL of ethanol was added 26.4 g (0.142 mole) of ethyl 2-ethoxymethyleneacetoacetate (combined Fractions 1-3 from Step B) in one portion. The resulting mixture was heated at reflux. After 1.5 hours about 5 g (0.03 mole) of ethyl 2-ethoxymethyleneacetoacetate was added. A second addition of approximately 1.5 g (0.0081 mole) of ethyl 2-ethoxymethyleneacetoacetate was made 1.25 hours later. After heating for an additional period, the reaction mixture was cooled, and the solvent was evaporated under reduced pressure, leaving a red oil weighing 48 g as a residue. This oil was dissolved in 225 mL of methylene chloride, and the resulting solution was washed successively with 10% hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and water. The solution was dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated under reduced pressure, leaving 35.4 g of 1-(3-chloro-5-trifluoromethyl-2-pyridyl)-4-ethoxycarbonyl-1H-5-methylpyrazole as a red oil. |
- 11
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[ 49836-24-0 ]
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[ 78703-53-4 ]
- 12
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[ 49836-24-0 ]
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[ 60-34-4 ]
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[ 85290-76-2 ]
Yield | Reaction Conditions | Operation in experiment |
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In ethanol; at 60℃; for 8h; |
A solution of ethyl acetoacetate (40 mmol) and triethyl orthoformate (60 mmol) in acetic anhydride (0.12 mol) was refluxed for 8 hours. After completion of the reaction, the product was distilled under reduced pressure to give crude product (1).Then, the intermediate (1) (40 mmol) was added dropwise to a mixture of methylhydrazine (60 mmol) and ethanol (20 mL) and reacted at 60 C for 8 hours. After completion of the reaction, the residue was distilled under reduced pressure, (20 mL) was extracted with saturated brine, and the organic layer was partitioned with anhydrous sodium sulfate and evaporated to give 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylate (2) The pyrazole ester 2 was stirred at room temperature for 12 hours in a solution of sodium hydroxide in ethanol. After removing the solvent ethanol, the solid was dissolved in water, hydrochloric acid was added, and a white solid 3 was precipitated.A solution of 14 g (0.1 mol) of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid (3) was charged into a 250 mL single-necked flask, 75 mL of SOCl2 was added slowly, heated under reflux for 4 h, and the reaction was complete by TLC. SOCl2 to give a pale yellow solid. 2.5 mmol of thiocyanate was dissolved in 15 ml of anhydrous acetonitrile, and then two drops of PEG-200 were added to the mixture, followed by stirring at room temperature for 5 min.Subsequently, 1 mmol of the acetonitrile solution of the compound 4 was added, and the mixture was stirred at room temperature for 40 minutes. The mixture was filtered to obtain an acetonitrile solution of pyrazolecarbonyl isothiocyanate and then substituted aniline (0.85 mmol) was added.After stirring at room temperature for 3-4 hours, the reaction mixture was evaporated in vacuo and the residue was subjected to silica gel column chromatography using petroleum ether and ethyl acetate as the solvent to give the product. |
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In ethanol; at 60℃; for 8h; |
The intermediate (1) (40 mmol) was then added dropwise to a mixture of methylhydrazine (60 mmol) and ethanol (20 mL) under ice-cooling to react at 60 C for 8 hours,After the reaction, vacuum distillation,Ethyl acetate (20 mL) was added and extracted with saturated brine,The organic layer was evaporated to dryness with anhydrous sodium sulfate,1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylate (2) |
- 13
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[ 22038-72-8 ]
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[ 49836-24-0 ]
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[ 85290-76-2 ]
Yield | Reaction Conditions | Operation in experiment |
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In ethanol; at 60℃; for 8h;Cooling with ice; |
Ethyl acetoacetate (40 mmol) and triethyl orthoformate (60 mmol) were refluxed in acetic anhydride (0.12 mol) for 8 hours. After completion of the reaction, the mixture was distilled under reduced pressure,(E) -2-ethoxymethylene-methyl-3-acetoacetic acid methyl ester represented by the formula (II) was obtained as a crude product; the obtained compound represented by the formula The compound (40 mmol) was dropped into a mixture of methylhydrazine (60 mmol) and ethanol (20 mL), and the mixture was reacted at 60 C for 8 hours. After the reaction was completed, the mixture was distilled under reduced pressure, extracted with ethyl acetate (20 mL) Dehydrating with anhydrous sodium sulfate followed by steaming gives ethyl (1-methyl-3-methyl-1H-pyrazole-4-carboxylate of formula (III) |
- 14
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[ 49836-24-0 ]
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[ 14527-26-5 ]
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[ 7234-25-5 ]
Yield | Reaction Conditions | Operation in experiment |
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With sodium acetate; In N,N-dimethyl-formamide; at 80℃; for 3.5h; |
To a solution of ethyl (2E)-2-(ethoxymethylene)-3-oxo-butanoate (50 g, 269 mmol) in DMF (dimethylformamide; 270 mL) was added sodium acetate (22 g, 269 mmol) and 2- methylisothiourea sulfate (50 g, 268 mmol). The mixture was stirred at 80 C for 3.5 hours. Upon completion, the mixture was cooled to room temperature (RT), then poured into ice water. Precipitation was formed, filtered and dried under reduced pressure to afford ethyl 4-methyl-2- methylsulfanyl-pyrimidine-5-carboxylate (47 g, crude) as a red solid, which was used in the next step without further purification. |
- 15
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[ 49836-24-0 ]
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[ 143-37-3 ]
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[ 2226-86-0 ]
Yield | Reaction Conditions | Operation in experiment |
50% |
With triethylamine In ethanol for 2h; Reflux; |
4.1 Step 1: Ethyl 2,4-dimethylpyrimidine-5-carboxylic acid(D-b)
(E) -2- (ethoxymethylene) -3-oxobutanoic acid ethyl ester Da (22 g, 0.12 mol) was added to a dry 250 mL single-necked flask, dissolved in ethanol (50 mL), and acetamidine ( 10 g, 0.11 mmol) and triethylamine (11 g, 0.11 mol). The reaction solution was heated to reflux and stirred for 2 hours. After the reaction was completed, the ethanol was spin-dried. Purification by column chromatography (ethyl acetate: petroleum ether = 9: 10) gave ethyl 2,4-dimethylpyrimidine-5-carboxylic acid D-b (10 g, 50% yield) as a brown oil. |