Alternatived Products of [ 21440-96-0 ]
Product Details of [ 21440-96-0 ]
| CAS No. : | 21440-96-0 |
MDL No. : | MFCD01664027 |
| Formula : |
C10H11NO2
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Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : | 177.20 g/mol |
Pubchem ID : | - |
| Synonyms : |
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Safety of [ 21440-96-0 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 21440-96-0 ]
* 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 [ 21440-96-0 ]
- Downstream synthetic route of [ 21440-96-0 ]
- 1
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[ 15833-00-8 ]
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[ 530-62-1 ]
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[ 21440-96-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 96% |
In 1,4-dioxane; at 20℃; for 2h; |
<strong>[15833-00-8]2-(2-aminophenyl)propan-2-ol</strong> (1.19 g, 7.87 mmol) was suspend in dioxane (10 mL) and added carbonyldiimidazole (1.53 g, 9.44 mmol) and stirred for 2 h at room temperature. Aqueous HCl (I N, 15 mL) was added and the reaction was extracted with ethyl acetate (3x20 mL). The combined organic layers were washed with IN HCl and brine, dried and concentrated to give 4,4-dimethyl-lH-3,l-benzoxazin-2-one as a pale solid (1.34 g, 7.56 mmol, 96%). The product was used as such without further purification in the next step LCMS: 0.70 min; ES+ 178 ( M+H+); lH NMR (CHLOROFORM-d, 400MHz): delta (ppm) 9.08 (br s, 1H), 7.24 (t, 1H), 7.14 (d, 1H), 7.07 (t, 1H), 6.89 (d, 1H), 1.73 (s, Step 3: 6-bromo-4.4-dimethyl-lH-3.1-benzoxazin-2-one |
| 92% |
In tetrahydrofuran; at 20℃; for 12h; |
2.2 Preparation of 4,4-Dimethyl-1,4-dihydrobenzoxazole-2-one 3.4 g of 2-(2-aminophenyl)-2-propanol and 5.5 g of CDI were added into 50 ml of anhydrous tetrahydrofuran and the mixture was reacted at room temperature for 12 hours; the reaction was quenched by adding 1M HCl solution and extracted with ethyl acetate. The organic phase was combined, washed with saturated aqueous sodium chloride, and the organic phase was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 3.7 g of a light yellow solid with a yield of 92%. 1HNMR (400 MHz, CDCl3): delta9.61 (s, 1H), 7.25 (m, 1H), 7.15 (d, 1H), 7.07 (m, 1H), 6.92 (dd, 1H), 1.74 (s, 6H) ppm. |
Reference：
[1]Patent: WO2018/17490,2018,A1 .Location in patent: Paragraph 0165; 0166
[2]Patent: US2019/84,2019,A1 .Location in patent: Paragraph 0264-0266
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 189 - 192
[4]Journal of Organic Chemistry,2020,vol. 85,p. 108 - 117
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[ 75-44-5 ]
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[ 15833-00-8 ]
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[ 21440-96-0 ]
| Yield | Reaction Conditions | Operation in experiment |
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In tetrahydrofuran; |
EXAMPLE 4; 1-{3-[2-hydroxy-2-(6-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-ethylamino]-3-methyl-butyl}-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one; a) 4,4-dimethyl-1,4-dihydro-benzo[1,3]oxazin-2-one; 112 g (1.13 mol) phosgene are piped into 500 mL THF. Then a solution of 52 g (0.34 mol) <strong>[15833-00-8]2-(2-amino-phenyl)-propan-2-ol</strong>, prepared from 2-aminoacetophenone and methylmagnesium iodide, in 300 mL THF is added. The reaction mixture is left to stand overnight, evaporated down and combined with 500 ml pyridine. After the pyridine has been distilled off water is added and the mixture is extracted with diethyl ether. The organic phases are washed successively with 2 N hydrochloric acid, sodium hydroxide solution and water, dried with sodium sulphate and evaporated down. The residue remaining (46 g) is further reacted directly without any more purification. |
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With methyl magnesium iodide; In tetrahydrofuran; |
112 g (1.13 mol) phosgene are piped into 500 mL THF. Then a solution of 52 g (0.34 mol) <strong>[15833-00-8]2-(2-amino-phenyl)-propan-2-ol</strong>, prepared from 2-aminoacetophenone and methylmagnesium iodide, in 300 mL THF is added. The reaction mixture is left to stand overnight, concentrated by evaporation and combined with 500 ml of pyridine. After the pyridine has been distilled off the remainder is combined with water and extracted with diethyl ether. The organic phases are washed successively with 2 N hydrochloric acid, sodium hydroxide solution and water, dried with sodium sulphate and concentrated by evaporation. The residue remaining (46 g) is further reacted directly, without any more purification. M.p. (toluene/petroleum ether)=109-110 C. |
| Yield | Reaction Conditions | Operation in experiment |
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EXAMPLE A 4,4-Dimethyl-4H-3,1-benzoxazin-2-one At 15-25 C. a solution of 226 g (1.5 mol) of methyl anthranilate in 1 liter of ether is added dropwise to a methyl magnesium iodide solution prepared from 170 g (7 mol) of magnesium chips, 993 g (7 mol) of methyl iodide in 3.5 liters of ether. After stirring for 1.5 hours the reaction mixture is poured onto ice water containing ammonium chloride, the ether phase is separated off, the aqueous phase is extracted again with ether and the combined ether phases are washed with ammonium chloride solution, dried with sodium sulphate and the ether is distilled off. The o-aminophenyldimethylcarbinol thus obtained is further reacted without being purified: |
- 4
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[ 21440-96-0 ]
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[ 21440-97-1 ]
| Yield | Reaction Conditions | Operation in experiment |
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With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 4h; |
4,4-dimethyl-lH-3,l-benzoxazin-2-one (1.00 g, 5.64 mmol) was dissolved in dimethylformamide (11 mL) and cooled to 0C. NBS (1.12 g, 6.21 mmol) was added. The reaction mixture was stirred at room temperature for 4 h.The reaction mixture was poured on water and the white precipitate was filtered and washed with water to give 6-bromo-4,4- dimethyl-lH-3,l-benzoxazin-2-one as a white powder (1.29 g, 89% LCMS: 0.83 min; ES+ 256/258 (M+H+); XH NMR (CHLOROFORM-d, 400MHz): delta (ppm) 9.13 (br s, 1H), 7.36 (d, 1H), 7.27 (s, 1H), 6.77 (d, 1H), 1.73 (s, 6H).yield). |
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