Alternatived Products of [ 1204-22-4 ]
Product Details of [ 1204-22-4 ]
CAS No. : | 1204-22-4 |
MDL No. : | MFCD03701176 |
Formula : |
C10H13ClO3
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
216.66
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 1204-22-4 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 1204-22-4 ]
* 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 [ 1204-22-4 ]
- Downstream synthetic route of [ 1204-22-4 ]
- 1
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[ 1204-22-4 ]
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[ 2785-98-0 ]
- 2
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[ 79-04-9 ]
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[ 150-78-7 ]
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[ 1204-22-4 ]
Yield | Reaction Conditions | Operation in experiment |
90.1% |
With Aluminum Chloride In dichloromethane at -20 - 20℃; for 24h; |
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85% |
With Aluminum Chloride In dichloromethane at 0 - 20℃; for 12.5h; |
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64% |
With hydrogenchloride In dichloromethane |
1.A Synthesis of 1-(2',5'-dimethoxyphenyl)-2-chloroethanone (Compound IV):
EXAMPLE 1A Synthesis of 1-(2',5'-dimethoxyphenyl)-2-chloroethanone (Compound IV): In a three-neck round bottom 2 liter flask, 60.0 g (0.434 mol) of 1,4-dimethoxybenzene is added. To the flask is added 300 mL dry dichloromethane to dissolve the solid. When the solution is clear, 63.7 g (0.477 mol) of anhydrous AlCl3 is added through a powder funnel and the funnel is washed with dichloromethane. The resulting solution is yellowish in color. This solution is stirred at room temperature for 5 minutes and 40.0 mL (0.50 mol) chloroacetylchloride in 5 mL dichloromethane is added dropwise (total addition time 1 hour 30 minutes) and is stirred vigorously at room temperature. The color of the solution became is orange-red and then like red wine. The solution is stirred for 4 hours after addition at room temperature and then poured in to a mixture of crushed ice and 126 mL conc. HCl and stirred for 20 minutes again. The organic phase is separated and the aqueous phase is extracted with CH2Cl2 (100 mL*3). Total dichloromethane fractions are combined and washed with H2O (100 mL*2), cold 10% aq. NaOH (200 mL*1) and H2O (100 mL*2) and dried over anhydrous sodium sulfate. The organic phase is evaporated under reduced pressure and the thick solution is cooled to room temperature yielding a yellow solid (59.0 g, yield 64%). The crude product is crystallized from methanol (m.p. 89-91° C.). |
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With aluminium chloride anhydrous In carbon disulfide |
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With Aluminum Chloride In dichloromethane at 20℃; for 12h; |
1 Example 1
Compound 1 (100 mg, 0.7 mmol) was dissolved in anhydrous dichloromethane (10 mL),The salt bath was added to chloroacetyl chloride (65.5 μL, 0.77 mmol) at -20°C, and the mixture was stirred for 10 min.Aluminum trichloride (108 mg, 0.78 mmol) was added in portions,Stir at room temperature for 12h and slowly pour the reaction mixture into crushed ice.Slowly drip in concentrated hydrochloric acid to adjust the pH to 2 with vigorous stirring.After stirring for 30min, add water, extract with dichloromethane (30mL×3), combine the organic layers, and wash.Saturated brine wash, dry anhydrous Na2SO4,After concentration, crude product target compound 2 (126 g, 81.1%) was obtained.The next step was carried out without purification. |
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With aluminium chloride anhydrous |
1 Example-1:
Example-1: 2-chloro-1-(2, 5-dimethoxyphenyl) ethane-1-one (VI) In a round bottom flask, 106.16 g of 2-chloroacetyl chloride was added into a mixture of 125.3 g of anhydrous aluminum chloride in 800 mL dichloromethane under nitrogen atmosphere at 25-35° C. and then stirred at 40-45° C. for 1-2 hours. The reaction mixture was cooled to 0-10° C. and a solution of 100 g 1,4-dimethoxy benzene in 400 mL dichloromethane was added and stirred for 10-12 hours at 25-35° C. After completion of the reaction, aqueous HCl was added into the reaction mixture and stirred for 1-2 hours. The organic layer was separated and washed with water, aqueous NaOH and brine and then the solvent was distilled out at reduced pressure to obtain the titled compound (129 g). |
129 g |
Stage #1: chloroacetyl chloride With Aluminum Chloride In dichloromethane at 0 - 42℃; Inert atmosphere;
Stage #2: 1,4-dimethoxybezene In dichloromethane at 0 - 23℃; Inert atmosphere; |
1; 5.1 Stage-1: Preparation of 2-chloro-1-(2,5-dimethoxyphenyl)ethan-1-one (VI)
In a round bottom flask, 600 mL dichloromethane, 96.50 g anhydrous AlCl3, were taken under nitrogen atmosphere and cooled to 0 to 10° C. 261.55 g chloro acetyl chloride was added and stirred for 15±5 minutes at 0 to 10° C. then the reaction mixture was stirred at 37 to 42° C. for 1-2 hours and then cooled to 0 to 10° C. A solution of 100 g 1, 4-dimethoxy benzene in 200 mL dichloromethane was added and stirred for 15±5 minutes at 0 to 10° C. The reaction mixture was stirred for 24 to 25 hour under nitrogen atmosphere at 17 to 23° C. After completion of the reaction, the reaction mixture was added into HCl in water and stirred at 0 to 20° C. for 15 to 20 minutes and then stirred at 25 to 35° C. for 20 to 25 minutes. The layers were separated and the organic layer was washed with sodium bicarbonate solution and then with water. The solvent was removed from the organic layer and 200 mL methanol was added into the reaction mixture at below 50° C. and stirred for 15 to 20 minutes and then it was removed under vacuum at below 50° C. Again 250 mL methanol was added at below 50° C. and the reaction mixture was stirred at 55 to 60° C. for 30 to 35 minutes. The reaction mixture was then cooled and stirred at 25 to 35° C. for an hour and then at 0 to 10° C. for an hour. The solid was filtered and washed with pre-cooled methanol and then dried under vacuum (Vacuum: NLT 700 mmHg) for 8 to 9 hours to obtain 2-chloro-1-(2,5-dimethoxyphenyl) ethan-1-one. |
Reference:
[1]Chen, Zhe-Sheng; Li, Dahong; Qiu, Yangyi; Wu, Liang; Xu, Jinyi; Xu, Shengtao; Yang, Dong-Hua; Yao, Hong; Zhou, Manzhen
[Journal of Medicinal Chemistry, 2021, vol. 64, # 23, p. 17346 - 17365]
[2]Fan, Hui-Lan; Li, Cheng-Ji; Luo, Sanzhong; Qin, Hong-Bo; Zhang, Da-Wei; Zhang, Wenzhao
[Chemical Communications, 2020, vol. 56, # 69, p. 10066 - 10069]
[3]Current Patent Assignee: NOVARTIS AG; Sandoz (in: Novartis) - US6201153, 2001, B1
[4]Sawada,S. et al.
[Chemical and pharmaceutical bulletin, 1977, vol. 25, p. 3370 - 3375]
[5]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN107365322, 2017, A
Location in patent: Paragraph 0098; 0100
[6]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - US2022/144754, 2022, A1
[7]Current Patent Assignee: ZYDUS LIFESCIENCES LTD - US2022/144754, 2022, A1
Location in patent: Paragraph 0151; 0153; 0157
- 3
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[ 1204-22-4 ]
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[ 75717-53-2 ]
Yield | Reaction Conditions | Operation in experiment |
88.8% |
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h; |
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84 mg |
With aluminum (III) chloride In dichloromethane at 20℃; for 12h; Cooling with ice; |
1 Example 1
Compound 2 (100 mg, 0.47 mmol) was dissolved in anhydrous dichloromethane (10 mL),Aluminum chloride (93.2 mg, 0.7 mmol) was added in portions under ice-water bath and stirred for 12 h at room temperature.Pour the reaction slowly into crushed ice.Slowly drip in concentrated hydrochloric acid to adjust pH to 2 and stir for 30 minutes before adding water.Dichloromethane extraction (30mL × 3), combined organic layer, washed with water,Saturated brine wash, anhydrous Na2SO4,Column chromatography after concentration (PE/EA 20:1, v/v) gave the target compound 3 (84 mg, 89.8%). |
Reference:
[1]Xu, Shengtao; Yao, Hong; Qiu, Yangyi; Zhou, Manzhen; Li, Dahong; Wu, Liang; Yang, Dong-Hua; Chen, Zhe-Sheng; Xu, Jinyi
[Journal of Medicinal Chemistry, 2021, vol. 64, # 23, p. 17346 - 17365]
[2]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN107365322, 2017, A
Location in patent: Paragraph 0098; 0101
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[ 1204-22-4 ]
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[ 39581-55-0 ]