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CAS No. : | 14267-92-6 | MDL No. : | MFCD00001014 |
Formula : | C5H7Cl | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 102.56 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210 | UN#: | 1993 |
Hazard Statements: | H225-H315 | Packing Group: | Ⅱ |
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 caesium carbonate; In N,N-dimethyl-formamide; at 20℃; | A mixture of Compound 1d (10.7 g, 0.052 mol), Compound 1b (7.10 g, 0.069 mol) and cesium carbonate (33.7 g, 0.10 mol) in DMF (40 mL) was stirred at room temperature overnight. The solid was filtered and washed with MeOH. The filtrate was evaporated, and the residue was dissolved in EtOAc. The solution was washed with H2O, brine, and dried (over Na2SO4) and concentrated to give the crude product. Flash chromatography purification (EtOAc/heptane, 1:5) afforded Compound 1e. 1H NMR (CDCl3): δ8.46 (m, 2H), 7.43 (m, 1H), 7.35 (m, 2H), 4.37 (t, J=6.7 Hz, 2H), 3.96 (s, 3H), 2.22 (m, 2H), 2.11 (m, 3H). ES-MS m/z 270 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 80℃; for 95h;Inert atmosphere; | Dimethyl iminodiacetate hydrochloride (2.9 g, 14.6 mmol), potassium carbonate (2.0 g, 14.6 mmol), and potassium iodide (2.4 g,14.6 mmol) were added to a solution of 5-chloro-1-pentyne (1.0 g,9.75 mmol) in DMF (5 mL). Under N2 stream, the mixture was stirred at 80 C for 95 hr. After the reaction, a saturated aqueous ammonium chloride solution was added to the mixture. Compounds were extracted with ethyl acetate, and the organic layer was dried with sodium sulfate. The solvent was removed under reduced pressure. Purification by silica gel flash-chromatography (hexane/ethyl acetate=1/1) yielded 9b(1.5 g, 6.6 mmol, 45%) as a colorless oil. 1H NMR (500 MHz, CDCl3) delta;3.70 (s, 6H), 3.55 (s, 4H), 2.82 (t, J=7.1 Hz, 2H), 2.26 (dt, J=7.1,2.7 Hz, 2H) 1.95 (t, J=2.7 Hz, 1H), 1.68 (quintet, J=7.1 Hz, 2H). 13CNMR (75 MHz, CDCl3) delta; 171.5, 83.8, 68.4, 54.7, 53.1, 51.3, 26.7, 15.7.MS (EI+) m/z; 227 ([M]+, 4.4), 168 (1 0 0). HRMS (EI+) m/z; 227.1150(Calcd: 227.1157 for C11H17NO4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate; potassium iodide; In 1-methyl-pyrrolidin-2-one; at 65℃; for 24h; | General procedure: A mixture of corresponding hydroxybenzonitrile 1a,c-i (1 mol),finely divided K2CO3 (5 mol), KI (0.01 mol), 5-chloro-1-pentyne(1.5 mol) and N-methylpyrrolidone-2 was heated at 65 C for24 h. The cooled reaction mixture was treated by cold water andstirred for 3e4 h. The solid was collected and recrystallized fromthe corresponding solvent. |