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[ CAS No. 120-25-2 ] {[proInfo.proName]}

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Chemical Structure| 120-25-2
Chemical Structure| 120-25-2
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Quality Control of [ 120-25-2 ]

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Product Details of [ 120-25-2 ]

CAS No. :120-25-2 MDL No. :MFCD00016614
Formula : C10H12O3 Boiling Point : -
Linear Structure Formula :C6H3(OCH3)(OCH2CH3)CHO InChI Key :BERFDQAMXIBOHM-UHFFFAOYSA-N
M.W : 180.20 Pubchem ID :67116
Synonyms :

Calculated chemistry of [ 120-25-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.62
TPSA : 35.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 1.63
Log Po/w (WLOGP) : 1.91
Log Po/w (MLOGP) : 1.13
Log Po/w (SILICOS-IT) : 2.34
Consensus Log Po/w : 1.82

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.06
Solubility : 1.56 mg/ml ; 0.00868 mol/l
Class : Soluble
Log S (Ali) : -1.99
Solubility : 1.85 mg/ml ; 0.0103 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.178 mg/ml ; 0.000989 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.48

Safety of [ 120-25-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 120-25-2 ]

* 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.

  • Downstream synthetic route of [ 120-25-2 ]

[ 120-25-2 ] Synthesis Path-Downstream   1~23

  • 2
  • [ 120-25-2 ]
  • [ 1071-36-9 ]
  • 3<i>t</i>-(3-methoxy-4-ethoxy-phenyl)-2-cyano-acrylic acid [ No CAS ]
  • 5
  • [ 120-25-2 ]
  • [ 93489-14-6 ]
  • <i>N</i>,<i>N</i>-bis-(4-ethoxy-3-methoxy-benzyl)-<i>N</i>'-phenyl-urea [ No CAS ]
  • 6
  • [ 18855-52-2 ]
  • [ 120-25-2 ]
  • [ 120-13-8 ]
  • 7
  • [ 22924-18-1 ]
  • [ 120-25-2 ]
  • [ 155048-12-7 ]
  • 8
  • [ 63-64-9 ]
  • [ 143-33-9 ]
  • [ 120-25-2 ]
  • [ 133765-45-4 ]
  • 9
  • [ 74-96-4 ]
  • [ 121-33-5 ]
  • [ 120-25-2 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;
92% Stage #1: vanillin With sodium hydroxide In water; isopropyl alcohol for 0.5h; Stage #2: ethyl bromide In water; isopropyl alcohol at 60℃; 1 Embodiment 1: Preparation of 4-ethoxy-3-methoxybenzaldehyde: 76 grams of 4-hydroxy-3-methoxybenzaldehyde (0.5mol) and 500mL of isopropanol are added into a four-necked flask and then stirred for 20 minutes, a constant pressure dropping funnel is used for slowly dropping 150 milliliters of aqueous solution of 6.5 grams of 18-crown-6 ether and 133 grams of sodium hydroxide, and stirring is performed for 30 minutes, the reaction system is heated to 60°C, at which 85 grams of bromethyl is dropped for reacting for 5 to 6 hours while TLC tracking is implemented, after the reaction ends, the reaction system is cooled (to 15°C) and is added with 500mL of water for stopped reaction, the product is extracted by ether (3x300mL), organic phase is washed with water to be neutral, anhydrous MgSO4 is dried, ether is partially distilled, a large amount of petroleum ether is added to precipitate crude product, the crude product is subjected to recrystallization by ether/petroleum ether to obtain 83 grams of 4-ethoxy-3-methoxybenzaldehyde:, and the yield is 92%.
91% Stage #1: vanillin With sodium hydroxide In water; isopropyl alcohol for 0.5h; Stage #2: ethyl bromide In water; isopropyl alcohol at 60℃; for 5 - 6h; 1 Synthesis of 4-ethoxy-3-methoxybenzaldehyde Example 1 Synthesis of 4-ethoxy-3-methoxybenzaldehyde A 1-liter four-necked flask fitted with thermometer, mechanical stirrer, and reflux condenser was charged with 62g 4-hydroxy-3-methoxybenzaldehyde (0.41mol) and 400ml isopropyl alcohol. The mixture was stirred for 20min, and then a 120ml water solution containing 5g 18-crown-6 ether and 106.3g sodium hydroxide (2.66ml) was gradually dropped thereto using a constant pressure funnel. After dropping, the mixture was stirred for 30min, and then heated to 60°C. At this temperature, 67.3g ethyl bromide (0.62mol) was introduced within 5-6 hours and the reaction was monitored with TLC. After the reaction finished, the mixture was cooled to 15°C, and 400ml water was then added to quench the reaction. The resulting mixture was extracted three times with ether (300 ml * 3). The organic layer was washed with water to pH=7, and dried with anhydrous magnesium sulfate. Part of the ether was removed by flash distillation and then large amount of petroleum ether was added to precipitate crude product. The crude product was recrystallized from diethyl ether/petroleum ether to give 67g 4-ethoxy-3-methoxybenzaldehyde in a yield of 91%. 1H-NMR (ppm) δ: 9.87 (1H, s; -CHO); 7.31 (1H, m; 2-ArH); 7.26 (1H, m; 6-ArH); 6.86 (1H, m; 5-ArH); 3.98 (2H, q; -CH2); 3.73 (3H, s; -OCH3); 1.42 (3H, t; -CH3). MS (m/Z): 180 (M+).
91% Stage #1: vanillin With sodium hydroxide In water; isopropyl alcohol for 0.5h; Stage #2: ethyl bromide In water; isopropyl alcohol at 60℃; for 5 - 6h; 1 Example 1 Synthesis of 4-ethoxy-3-methoxybenzaldehyde A 1-liter four-necked flask fitted with thermometer, mechanical stirrer, and reflux condenser was charged with 62 g 4-hydroxy-3-methoxybenzaldehyde (0.41 mol) and 400 ml isopropyl alcohol. The mixture was stirred for 20 min, and then a 120 ml water solution containing 5 g 18-crown-6 ether and 106.3 g sodium hydroxide (2.66 mol) was gradually dropped thereto using a constant pressure funnel. After dropping, the mixture was stirred for 30 min, and then heated to 60° C. At this temperature, 67.3 g ethyl bromide (0.62 mol) was introduced within 5-6 hours and the reaction was monitored with TLC. After the reaction finished, the mixture was cooled to 15° C., and 400 ml water was then added to quench the reaction. The resulting mixture was extracted three times with ether (300 ml*3). The organic layer was washed with water to pH=7, and dried with anhydrous magnesium sulfate. Part of the ether was removed by flash distillation and then large amount of petroleum ether was added to precipitate crude product. The crude product was recrystallized from diethyl ether/petroleum ether to give 67 g 4-ethoxy-3-methoxybenzaldehyde in a yield of 91%. 1H-NMR (ppm) δ: 9.87 (1H, s; -CHO); 7.31 (1H, m; 2-ArH); 7.26 (1H, m; 6-ArH); 6.86 (1H, m; 5-ArH); 3.98 (2H, q; -CH2); 3.73 (3H, s; -OCH3); 1.42 (3H, t; -CH3). MS (m/Z): 180 (M+).
90% With potassium carbonate In acetone for 8h; Heating;
With potassium carbonate In acetone
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h;
With potassium carbonate In acetone for 24h; Reflux; 8.70.1 To a mixture of A (2.0 g, 13.1 mmol) and K2CO3 (2.17 g, 15.7 mmol) in 100 mL of acetone, CHsCHiBr (1.5 mL, 20.0 mmol) was added. After heating at reflux temperature for one day, the reaction mixture was cooled down. Acetone was removed. Then the reaction mixture was diluted with DCM, washed with water, dried over anhydrous Na2SO4, the solvent evaporated and the residue purified on silica chromatography with eluent (EtOAc: PE= 1 :8) to afford 2.49 g of B.
With potassium carbonate In acetone for 24h; Reflux; 2.31 31. Preparation of Compound 113; A to B; To a mixture of A (2.0 g, 13.1 mmol) and K2CO3 (2.17 g, 15.7 mmol) in 100 mL of acetone, CH3CH2Br (1.5 mL, 20.0 mmol) was added. After heating at reflux temperature for one day, the reaction mixture was cooled down. Acetone was removed. Then the reaction mixture was diluted with DCM, washed with water, dried over anhydrous Na2SO4, the solvent evaporated and the residue purified on silica chromatography with eluent (EtOAc: PE=1:8) to afford 2.49 g of B.
Stage #1: vanillin With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 0.166667h; Stage #2: ethyl bromide In N,N-dimethyl-formamide at 70℃; 5-(3-(Benzyloxy)-4-ethoxystyryl)-1,2,3-trimethoxybenzene (sit-11) (Scheme 1): A mixture of 4-hydroxy-3-methoxybenzaldehyde 1 (1g, 6.57mmol) and potassium carbonate (1.36g, 9.85mmol) in DMF (20mL) was stirred at 40°C for 10min. Ethyl bromide (0.98mL, 13.1mmol) was added through the septum after the mixture was raised to 70°C. The reaction mixture was then stirred at this temperature until TLC analysis indicated the completion of the reaction, then quenched by water, extracted with EtOAc, dried over Na2SO4 and concentrated. Pure white 4-ethoxy-3-methoxybenzaldehyde 2 was obtained by crystallization (petroleum ether (60-90°C): EtOAc=9:1, v/v). mp 62.1-62.2°C. 1H NMR (CDCl3, 500MHz): δ 9.84 (s, 1H), 7.41-7.45 (m, 2H), 6.96 (d, 1H, J=5.0Hz), 5.80 (s, 1H), 4.19 (q, 2H, J=5.0Hz), 3.93 (s, 3H), 1.50 (t, 3H, J=5.0Hz).
Stage #1: vanillin With potassium carbonate In N,N-dimethyl-formamide at 60 - 65℃; for 0.5h; Stage #2: ethyl bromide In N,N-dimethyl-formamide at 80℃; Inert atmosphere; 2.2. Synthesis of a chalcone derivative (1v) In a 100 mL two neck-round bottom flask equipped with refluxcondenser containing DMF (10 mL) was added 4-hydroxy-3-methoxybenzaldehyde (2 g, 0.01 mol) and anhydrous K2CO3(2.07 g, 0.015 mol) and heated the reaction mixture at 60e65 C for30 min before the dropwise addition of bromoethane (0.01 mol).After addition of bromoethane, the whole reaction mixture washeated under N2 at 80 C for 4e5 h. After the completion of thereaction, monitored by TLC, the reaction mixture was poured intoseparating funnel containing ethylacetate and washed severaltimes with water. The organic layer was then dried over anhydrousMgSO4, evaporated by using rotary evaporator to get 4-ethoxy-3-methoxybenzaldehyde intermediate, which was used in the nextstep without further purification. The 4-Alkoxy-3-methoxybenzaldehyde intermediate (0.01 mol, 1 g) was dissolvedin ethanol (10 mL) in a 100 mL round bottom flask and 37% icecooled NaOH solution (10 mL) was then added into it. After stirringthe reaction mixture for 30 min at 0 C, the acetophenone(0.01 mol) was added dropwise and stirred for another 4e6 h. Theprecipitates thus appeared were poured into the crushed ice,filtered and washed thoroughly with water. The obtained solid wasfinally recrystallized from ethanol to get pure 1v.
With potassium carbonate In acetonitrile Reflux; 20.2 (2) vanillin (5.0 mmol), potassium carbonate (15.0 mmol) and ethyl bromide (6.0 mmol),30mL of acetonitrile is used as a solvent, added to a 100mL three-necked bottle, and refluxed for 3-5h.The reaction progress was followed by TLC. After the reaction was completed, the reaction was stopped, washed with ice water, and then the solid intermediate 4-ethoxy-3-methoxybenzaldehyde was collected by filtration;...
2.49 g With potassium carbonate In acetone for 24h; Reflux; 8.70.1 A to B [00285] To a mixture of A (2.0 g, 13.1 mmol) and K2CO3 (2.17 g, 15.7 mmol) in 100 mL of acetone, CTLCrLBr (1.5 mL, 20.0 mmol) was added. After heating at reflux temperature for one day, the reaction mixture was cooled down. Acetone was removed. Then the reaction mixture was diluted with DCM, washed with water, dried over anhydrous Na2SC>4, the solvent evaporated and the residue purified on silica chromatography with eluent (EtOAc: PE= 1 :8) to afford 2.49 g of B.

Reference: [1]Doušová, Hana; Růžičková, Zdeňka; Šimůnek, Petr [Journal of Heterocyclic Chemistry, 2018, vol. 55, # 3, p. 670 - 684]
[2]Current Patent Assignee: ZHEJIANG WILDWIND PHARMACEUTICAL; SHANGHAI ECUST BIOMEDICINE - EP2351730, 2011, A1 Location in patent: Page/Page column 9
[3]Current Patent Assignee: ZHEJIANG DADE PHARMACEUTICAL GROUP CO., LTD.; ZHEJIANG DADE PHARMACEUTICAL G - EP2065358, 2009, A1 Location in patent: Page/Page column 10-11; 19
[4]Current Patent Assignee: ZHEJIANG DADE PHARMACEUTICAL GROUP CO., LTD.; ZHEJIANG DADE PHARMACEUTICAL G - US2009/170956, 2009, A1 Location in patent: Page/Page column 7; fig.1
[5]Del Carmen Cruz, María; Tamariz, Joaquín [Tetrahedron, 2005, vol. 61, # 42, p. 10061 - 10072]
[6]Chowdhury; Saxena; Walia [Journal of Agricultural and Food Chemistry, 1998, vol. 46, # 2, p. 731 - 736]
[7]Lebedev; Lebedeva; Sheludyakov; Kovaleva; Ustinova; Kozhevnikov [Russian Journal of General Chemistry, 2005, vol. 75, # 7, p. 1113 - 1124]
[8]Current Patent Assignee: CVI PHARMACEUTICALS - WO2010/75469, 2010, A1 Location in patent: Page/Page column 118
[9]Current Patent Assignee: CVI PHARMACEUTICALS - US2011/9628, 2011, A1 Location in patent: Page/Page column 40-41
[10]Zhao, Lei; Zhou, Jiu-Jiu; Huang, Xin-Ying; Cheng, Li-Ping; Pang, Wan; Kai, Zhen-Peng; Wu, Fan-Hong [Chinese Chemical Letters, 2015, vol. 26, # 8, p. 993 - 999]
[11]Anam, Faiza; Abbas, Asghar; Lo, Kong Mun; Hameed, Shahid; Ramasami, Ponnadurai; Umar, Yunusa; Ullah, Aman; Naseer, Muhammad Moazzam [Journal of Molecular Structure, 2017, vol. 1127, p. 742 - 750]
[12]Current Patent Assignee: GUIZHOU UNIVERSITY - CN109651365, 2019, A Location in patent: Paragraph 0149; 0151
[13]Current Patent Assignee: CVI PHARMACEUTICALS - WO2021/67490, 2021, A1 Location in patent: Paragraph 00285
  • 10
  • [ 141-82-2 ]
  • [ 120-25-2 ]
  • [ 54503-18-3 ]
  • [ 144878-40-0 ]
YieldReaction ConditionsOperation in experiment
1: 64% 2: 19% With ammonium acetate In butan-1-ol Heating;
  • 11
  • [ 120-25-2 ]
  • [ 103095-48-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium/charcoal; ethanol / Hydrogenation 2: acetic acid; concentrated aqueous HNO3 3: KMnO4
  • 12
  • [ 120-25-2 ]
  • [ 838814-43-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; bromine 2: aqueous potassium permanganate solution
  • 13
  • [ 2645-07-0 ]
  • [ 120-25-2 ]
  • [ 855414-02-7 ]
YieldReaction ConditionsOperation in experiment
30% With sodium acetate; acetic anhydride for 2h; Heating;
  • 16
  • [ 13078-21-2 ]
  • [ 120-25-2 ]
  • C21H26O7 [ No CAS ]
  • C21H26O7 [ No CAS ]
  • 17
  • [ 145-13-1 ]
  • [ 120-25-2 ]
  • [ 1365727-41-8 ]
YieldReaction ConditionsOperation in experiment
95% With potassium hydroxide In ethanol at 20℃; General procedure: To a solution of 1 (100 mg, 0.316 mmol) in 95% EtOH (10 mL) was added solid KOH (35 mg, 0.632 mmol) and aldehyde (1.2 equiv). The mixture was stirred at room temperature for 24-48 h, then the reaction was quenched with 10% HCl. The reaction mixture was extracted with ethyl acetate (3×15 mL). The organic layers were combined, washed with brine (3×10 mL), dried over anhydrous MgSO4, filtered, and concentrated. The residue was subjected to silica gel chromatographic with petroleum ether/EtOAc (4:1 to 3:1) to give 2.
  • 18
  • [ 5440-00-6 ]
  • [ 120-25-2 ]
  • [ 578756-83-9 ]
YieldReaction ConditionsOperation in experiment
75% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In water; acetonitrile at 30 - 35℃; for 2h; 4.2. Typical synthetic procedure for 8-substituted xanthines General procedure: In a round bottom flask, 5,6-diamino-1,3-dimethyluracil (0.425 g, 2.5 mmol, 1 equiv) and aryl/cycloaryl/heteroaryl aldehyde (2.5 mmol, 1 equiv) was stirred in CH3CN/H2O (9:1) (10 mL) for 15 min. To this, catalytic amount (0.008 g, 0.05 mmol, 0.02 equiv) of AIBN was added and after stirring for 5 min, 0.7 equiv of NBS (in two portions, initially 0.5 equiv and after 30 min additional 0.2 equiv) (0.311 g, 1.75 mmol) was added and the reaction mixture was stirred at room temperature (30-35 °C). The reaction progress was monitored by TLC (dichloromethane/methanol=19:1) as well as HPLC. After the reaction was completed, the resulting precipitate was filtered under vacuum and the precipitate was washed with ethyl acetate (2×10 mL) and methanol (3×10 mL) to obtain the pure product.
  • 19
  • [ 120-25-2 ]
  • [ 2476-29-1 ]
  • [ 1448349-05-0 ]
  • 20
  • [ 120-25-2 ]
  • [ 498-02-2 ]
  • (E)-3-(4-ethoxy-3-methoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydroxide In methanol at 20℃; for 72h; Inert atmosphere; General Experimental Procedure for the Synthesis ofChalcone Derivatives (1a-1l) General procedure: To a methanol solution containing apocynin (300 mg,1.80 mmol) was added sodium hydroxide (7.20 mmol) followedby the addition of benzaldehydes (a-l) (1.90 mmol)and the contents were stirred at room temperature for 24h-72h. The reaction mixture was diluted with water and acidifiedto pH = 3 using 1N HCl and extracted with ethyl acetate.The organic layer was washed with water followed bybrine solution, dried over anhydrous sodium sulphate, filteredand concentrated under reduced pressure, to obtain thepure compounds. Yields of the products varied between 78and 98%.
  • 21
  • [ 1271-55-2 ]
  • [ 120-25-2 ]
  • 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: acetylferrocene; 4-ethoxy-3-methoxybenzaldehyde In ethanol for 0.166667h; Stage #2: With sodium hydroxide In ethanol at 50℃; General procedure for synthesis of chalcones General procedure: The corresponding vanillin aldehyde 2a-f (10 mmol) and acetylferrocene (10 mmol) were dissolved in 20 mL of warm ethanol, and the mixture was stirred for 10 min and1 mL of 40% NaOH was added slowly. The reaction mixture was stirred overnight at 50°C. Crushed ice, 100 g, was placed in a beaker and the reaction mixture was poured onto it with stirring. The product in some cases could be isolated by filtration, if not it was necessary to extract with toluene or dichloromethane (3 ×50 mL). The organic layerwas washed with water (2 ×50 mL), brine (2 ×50 mL), and dried over anhydrous Na2SO4. The main part of the solvent was evaporated at reduced pressure and crude concentrated solution was filtered through a short column of silica gel. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel column using toluene-ethyl acetate (8:2) mixture as eluent for separation of reaction products 3a-f.
With sodium hydroxide In ethanol at 50℃;
  • 22
  • [ 120-25-2 ]
  • [ 78364-55-3 ]
  • C17H16FN3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 70 - 80℃; for 3h; General procedure: The mixture of <strong>[78364-55-3]6-fluoro-2-hydrazinylbenzo[d]thiazole</strong> (2) (0.01 mol) and benzalde-hyde/substituted benzaldehyde (0.01 mol) was reuxed in ethanol (15 ml) at 70?80 °C for 3 h. The separated product obtained was ltered off, washed withdistilled water and recrystallized from methanol to give the correspondinghydrazone. The product obtained was further dissolved in acetic acid (20 ml) atroom temperature followed by the addition of sodium acetate (0.5 g). Bromine(2 mmol) in acetic acid (10 ml) was added dropwise to the reuxing reactionmixture. After 1 h, the mixture was poured onto crushed ice (100 g). The precipitateobtained was ltered off and crystallized from ethanol-dimethylformamide (1:1) togive crystals of (3a?3t).
  • 23
  • [ 611-17-6 ]
  • [ 120-25-2 ]
  • [ 17356-08-0 ]
  • [ 105-56-6 ]
  • 2-((2-chlorobenzyl)thio)-4-(4-ethoxy-3-methoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 1-bromomethyl-2-chlorobenzene; thiourea In ethanol at 85℃; for 4h; Inert atmosphere; Stage #2: 3-methoxy-4-ethoxybenzaldehyde; ethyl 2-cyanoacetate With sodium hydroxide In methanol at 70℃; for 5h; Inert atmosphere; 5.11.1. General procedure a for the synthesis of A2,A22-A31 General procedure: A1-a or A1-b (34.16 mmol), different halides (31.05 mmol), and 60ml ethanol were added to a 250 ml round bottom flask and protected by nitrogen. The mixture was heated to 85 C and refluxed for 4 h. Thereaction was detected by TLC until it was completely finished. Then theround bottom flask was removed from the oil bath and cooled to roomtemperature. The mixture was stirred slowly in the ice bath for 2 h toprecipitate a large amount of white crystalline powder. The solid wasfiltered and triturated with EtOH to give the target compound as whitepowder (Y = 61.0%-84.6%). 5.11.2. General procedure B for the synthesis of 1-18,23-34A2, A27-A38 (1.0 mmol), different benzaldehydes (1.0 mmol), ethylcyanoacetate (106.51 mg, 1.0 mmol), NaOH (44.16 mg, 1. 1 mmol) and10 ml methanol were added into a 25 ml round bottom flask under nitrogenprotection and heated to 70 C for 5 h. The reaction was detectedby TLC until it was completely finished. After cooling to room temperature,the mixture was concentrated under vacuum and the residueobtained was purified by column chromatography to give the targetcompound.
63% Stage #1: 1-bromomethyl-2-chlorobenzene; thiourea In ethanol at 85℃; for 4h; Inert atmosphere; Stage #2: 3-methoxy-4-ethoxybenzaldehyde; ethyl 2-cyanoacetate With sodium hydroxide In methanol at 70℃; for 5h; Inert atmosphere; 5.11.1. General procedure a for the synthesis of A2,A22-A31 General procedure: A1-a or A1-b (34.16 mmol), different halides (31.05 mmol), and 60ml ethanol were added to a 250 ml round bottom flask and protected by nitrogen. The mixture was heated to 85 C and refluxed for 4 h. Thereaction was detected by TLC until it was completely finished. Then theround bottom flask was removed from the oil bath and cooled to roomtemperature. The mixture was stirred slowly in the ice bath for 2 h toprecipitate a large amount of white crystalline powder. The solid wasfiltered and triturated with EtOH to give the target compound as whitepowder (Y = 61.0%-84.6%). 5.11.2. General procedure B for the synthesis of 1-18,23-34A2, A27-A38 (1.0 mmol), different benzaldehydes (1.0 mmol), ethylcyanoacetate (106.51 mg, 1.0 mmol), NaOH (44.16 mg, 1. 1 mmol) and10 ml methanol were added into a 25 ml round bottom flask under nitrogenprotection and heated to 70 C for 5 h. The reaction was detectedby TLC until it was completely finished. After cooling to room temperature,the mixture was concentrated under vacuum and the residueobtained was purified by column chromatography to give the targetcompound.
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