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CAS No. : | 124-68-5 | MDL No. : | MFCD00008051 |
Formula : | C4H11NO | Boiling Point : | - |
Linear Structure Formula : | OHCH2C(CH3)2NH2 | InChI Key : | CBTVGIZVANVGBH-UHFFFAOYSA-N |
M.W : | 89.14 | Pubchem ID : | 11807 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P264-P273-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P363-P405-P501 | UN#: | 1760 |
Hazard Statements: | H303-H314-H412 | Packing Group: | Ⅲ |
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 |
---|---|---|
72% | In pentan-1-ol;Heating / reflux; | (d) 6-Chloro-3-nitro-2-picoline (6.055 g, 35.1 mmol) and 2-amino-2-methyl-propan-1-ol (6.2 g, 73.7 mmol) were suspended in 1-pentanol (30 ml) and the mixture refluxed under inert atmosphere overnight The thin layer chromatography (dichloromethane 4/EtOAc 1) revealed some remaining starting material, so the reaction was refluxed for another 3.5 hrs. The reaction mixture was cooled and water was added under stirring. A sticky, yellow precipitate was filtered off, washed well with water and dried. The crude product (6.04 g) was re-crystallised from either pentane-acetone or dichloromethane. Collecting the crops furnished 5.71 (72 percent) of 2-methyl-2- (6-methyl-5-nitro-pyridin-2-ylamnio- propan-l-ol as yellow crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With sodium hydroxide; In water; at 20℃; for 16h; | To a stirred solution of 2-amino-2-methyl-1-propanol (3.48 g, 39 mmol) in 1N NaOH (25 ml) was added at room temperature 4-chloro-3-nitrobenzenesulfonyl chloride (5.0 g, 19.5 mmol). The reaction mixture was stirred at room temperature for 16h, poured into brine (50 ml) and extracted with ethyl acetate (3 x 70 ml). The combined organic layers were washed with brine (50 ml), dried (MgS04) and evaporated. The crude product was further purified by column chromatography on silica gel (heptane/ ethyl acetate 1:4) and subsequent crystallization from ethyl acetate/ heptane to yield 4-chloro-3-nitro-(2- hydroxy-1,1-dimethyl-ethyl)-benzenesulfonamide (0.93 g, 15%) as an off-white solid. MS (ISP) 307.0 [(M-H)-]; mp 119C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; water; ethyl acetate; | (1) To a suspension of 0.43 g of 60% (w/w) sodium hydride in 15 ml of tetrahydrofuran is added a solution of 0.80 g of 2-amino-2-methyl-1-propanol in 20 ml of tetrahydrofuran at 20-25 C., and they are refluxed for two hours. To the reaction mixture is added a solution of 2.36 g of <strong>[16263-53-9]3,5-dichloro-1,2-benzoisoxazole</strong> in 20 ml of tetrahydrofuran under reflux, and they are refluxed for a further one hour. After cooling, the solvent is removed by distillation under reduced pressure, and ethyl acetate and water are added to the residue obtained, and after shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution, dried over anhydrous magnesium sulfate and then purified by a column chromatography [eluant:chloroform:methanol=20:1], to obtain 1.59 g of oily 3-(2-amino-2-methylpropoxy)-5-chloro-1,2-benzoisoxazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
197 mg | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 4.0h;Inert atmosphere; | 2-tert-Butoxycarbonylamino-4,5,6,7-tetrahydro-benzo[]thiophene-3-carboxylic acid (200 mg, prepared according Y. Huang et al, Chem. Biol. Drug Des. 2010, 76, 116-129) was dissolved in DMF (5 mL) at RT under argon. Then HATU (264 mg), DIPEA (88.7 mg) and 2- amino-2-methylpropan-l-ol (63.1 mg) were added and the reaction solution was stirred at RT for 4 h until TLC (n-heptane/EtOAc: 1/1) indicated completion of the reaction. The reaction mixture was diluted with H20 and extracted with EtOAc. The combined organic layers were washed with 2M aqueous KHCO3 solution, dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/n-heptane, gradient from 0 to 25%) to give the desired compound as a colorless solid (197 mg). MS (ESI): m/z = 369.1 [M+H] +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With zinc(II) triflate; In chlorobenzene; at 135℃; for 24h;Inert atmosphere; | General procedure: A 50 mL round bottom flask equipped with a reflux condenser was charged with the appropriate amount of the substituted phthalonitrile (4.0 mM), zinc triflate (5.0 M%, 0.20 mM), and chlorobenzene (30 mL) under argon. The mixture was stirred to dissolve the phthalonitrile and then 2-aminoalcohol (8.0 mM), dissolved in dry chlorobenzene, was slowly added. The temperature was raised to 135 C and the reaction mixture was refluxed for 24 h. The product of the reaction, which was obtained as an oily residue, was dissolved in 30 mL of dichloromethane and then extracted twice with distilled water (20 mL). The aqueous layer was separated and washed with dichloromethane. The separated organic layers were dried using anhydrous sodium sulfate. The dichloromethane was removed under vacuum on a rotary evaporator to give the crude product, which was then purified using silica gel column chromatography with dichloromethane/ether (4/1) as eluent [14, 16, 17]. |
87% | With zinc trifluoromethanesulfonate; In chlorobenzene; for 24h;Reflux; | A solution of phthalonitrile derivative and zinc triflate in drychlorobenzene was stirred at room temperature for15 min, and then a solution of aminoalcohol in dry chlorobenzene was slowly added. The temperature was raised to 135C, and the reaction mixture was refluxed for 24 h. |
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