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CAS No. : | 3697-66-3 | MDL No. : | MFCD08690114 |
Formula : | C7H10O4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | QQUZUWSSLUHHBP-UHFFFAOYSA-N |
M.W : | 158.15 | Pubchem ID : | 11789472 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
With hydrogenchloride; triethylamine; In dichloromethane; water; acetonitrile; | EXAMPLE XXXIII Preparation of ethyl 1-(4-chloro-2-ethylphenylaminocarbonyl)cyclopropinecarboxylate To a stirred solution of 1.54 grams (0.01 mole) of 1-carboethoxycyclopropanecarboxylic acid (the monocarboxylic acid intermediate described in Example XVIII) and 0.99 gram (0.01 mole) of triethylamine in 75 milliliters of acetonitrile was added a solution of 1.06 grams (0.01 mole) of ethyl chloroformate in 25 milliliters of acetonitrile dropwise with cooling to 0 C.-5 C. After stirring at ice temperature for 30 minutes a solution of 1.52 grams (0.01 mole) of <strong>[30273-39-3]4-chloro-2-ethylaniline</strong> in 20 milliliters of acetonitrile was fed dropwise with stirring and continued cooling. The reaction mixture was allowed to warm to room temperature, then stirred for approximately sixteen hours following which it was filtered and the filtrate freed of solvent by evaporation. The residue was dissolved in dichloromethane and extracted, successively, with water (2*50 milliliters), 2N HCl (2*50 milliliters) and water (1*50 milliliters). After drying (MgSO4), solvent was removed by evaporation and the solid recrystallized from hexane to give 1.15 grams (0.004 mole) of ethyl 1-(4-chloro-2-ethylphenylaminocarbonyl)cyclopropanecarboxylate as cream colored prisms having a melting point of 77 C.-80 C. Elemental analysis of the product indicated the following: Analysis: C15 H18 ClNO3 Calculated: C, 60.91; H, 6.13; Found: C, 61.38; H, 6.13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With hydrogen fluoride; In dichloromethane; | Ethyl 1-trifluoromethylcyclopropanecarboxylate STR20 31.6 g (0.20 mol) of monoethyl cyclopropane-1,1-dicarboxylate, 126 g (1.16 mol) of sulfur tetrafluoride, 100 ml of dichloromethane and 1.5 g (75 mmol) of hydrogen fluoride were introduced at -70 C. into a 500 ml stirred autoclave which was lined with an alloy of 70% of nickel, 15% of chromium and 15% of molybdenum. The mixture was heated for 48 hours at 80 C. and the gaseous constituents were destroyed, after cooling the autoclave to 35 C., by passing them into a wash tower filled with potassium hydroxide. The residue was dissolved in 100 ml of dichloromethane. The solution was washed with 100 ml of saturated sodium bicarbonate solution, after which the organic phase was dried with sodium sulfate and potassium fluoride and was separated into the individual components by distillation. Yield: 76%; bp.: 141-142 C.; oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; triethylamine; In dichloromethane; water; acetonitrile; | EXAMPLE XXXIII Preparation of ethyl 1-(4-chloro-2-ethylphenylaminocarbonyl)cyclopropanecarboxylate To a stirred solution of 1.54 grams (0.01 mole) of 1-carboethoxycyclopropanecarboxylic acid (the monocarboxylic acid intermediate described in Example XVIII) and 0.99 gram (0.01 mole) of triethylamine in 75 milliliters of acetonitrile was added a solution of 1.06 grams (0.01 mole) of ethyl chloroformate in 25 milliliters of acetonitrile dropwise with cooling to 0 C.-5 C. After stirring at ice temperature for 30 minutes a solution of 1.52 grams (0.01 mole) of <strong>[30273-39-3]4-chloro-2-ethylaniline</strong> in 20 milliliters of acetonitrile was fed dropwise with stirring and continued cooling. The reaction mixture was allowed to warm to room temperature, then stirred for approximately sixteen hours following which it was filtered and the filtrate freed of solvent by evaporation. The residue was dissolved in dichloromethane and extracted, successively, with water (2*50 milliliters), 2N HCl (2*50 milliliters) and water (1*50 milliliters). After drying (MgSO4), solvent was removed by evaporation and the solid recrystallized from hexane to give 1.15 grams (0.004 mole) of ethyl 1-(4-chloro-2-ethylphenylaminocarbonyl)cyclopropanecarboxylate as cream colored prisms having a melting point of 77 C.-80 C. Elemental analysis of the product indicated the following: Analysis: C15 H18 ClNO3; Calculated: C, 60.91; H, 6.13. Found: C, 61.38; H, 6.13. |
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