17641-08-6|2-Chloro-N-(3-methoxyphenyl)acetamide| Ambeed

Structure of 17641-08-6

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Quality Control of [ 17641-08-6 ] Purity: 98% SDS Specification

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Product Details of [ 17641-08-6 ]

CAS No. :	17641-08-6
Formula :	C₉H₁₀ClNO₂
M.W :	199.63
SMILES Code :	O=C(NC1=CC=CC(OC)=C1)CCl
MDL No. :	MFCD00018900
InChI Key :	JJNAIBJFYFWTIA-UHFFFAOYSA-N
Pubchem ID :	28667

Safety of [ 17641-08-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P264-P270-P301+P312-P330-P501

Computational Chemistry of [ 17641-08-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	52.04
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.33 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.64
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.92
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.68
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.54
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.9
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.74

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.36
Solubility	0.862 mg/ml ; 0.00432 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.35
Solubility	0.895 mg/ml ; 0.00448 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.55
Solubility	0.0561 mg/ml ; 0.000281 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.15 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.53

Application In Synthesis of [ 17641-08-6 ]

* 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 [ 17641-08-6 ]

[ 17641-08-6 ] Synthesis Path-Downstream 1~35

1
[ 110-89-4 ]
[ 17641-08-6 ]
[ 40297-47-0 ]

References: [1]Pharmaceutical Chemistry Journal,1981,vol. 15,p. 849 - 853.
Khimiko-Farmatsevticheskii Zhurnal,1981,vol. 15,p. 23 - 26.
[2]Journal of the Indian Chemical Society,1940,vol. 17,p. 400,401.

2
[ 536-90-3 ]
[ 79-04-9 ]
[ 17641-08-6 ]

Yield	Reaction Conditions	Operation in experiment
91.5%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 1h;Inert atmosphere;	To a solution of compound A (0.5 g, 4.05 mmoles) in ACN (10.0 mL) was added DIPEA (1.56 mL, 8.93 mmoles) , followed by dropwise addition of compound B (0.387 mL, 4.87 mmoles) under argon atmosphere. After the addition was complete the reaction was stirred at rt for 1 hour. The completion of the reaction was monitored by TLC. The reactionmixture was concentrated, purified by column chromatography (20 %EtOAc:Hexanes) to isolate the required compound as brown solid (0.74 g, 91.5%). 1H NMR (CDCl3, 400 MHz) δ 8.30 ( s, 1 H),7.28-7.23(m, 2 H), 7.03 (d, J=7.6 Hz, 1 H), 6.74-6.70(m, 1 H), 4.18 (s, 2 H), 3.81 (s, 3 H).
80.7%	With pyridine; In dichloromethane; at 0 - 20℃; for 12h;	Example 34 IV-1 6-(4-(4-(3-(6-fluoro-benzisoxazolyl))-1-piperidinyl)-n-butoxy)-indoline-2-one 1) 2 ml of pyridine is added to 30 ml of a solution of 3-methoxyaniline (4.92g, 40 mmol) in dichloromethane and the mixture is stirred for 5 minutes, while maintaining the temperature inside vessel at lower than 0C, and thereto 20 ml of a solution of chloroacetyl chloride (6.78g, 60 mmol) in dichloromethane is drop-added slowly. A reaction is carried out at room temperature for 12 hours after completion of drop-addition, and then terminated. The reaction solution is washed with 5% of HCl (30ml×3), 5% of NaOH (30ml×3), water (30ml×3), and saturated saline (30 ml) successively, dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated to remove the solvent to obtain 6.43g of 2-chloro-N-(3-methoxyphenyl)acetamide , with a yield of 80.7%.
80.7%	With pyridine; In dichloromethane; at 0 - 20℃; for 12h;	2 ml of pyridine was added to 30 ml of a dichloromethane solution of 3-methoxyaniline (4.92 g, 40 mmol), and the mixture was stirred for 5 minutes. While maintaining the internal temperature at 0 C, a solution of chloroacetyl chloride (6.78 g, 60 mmol) in dichloromethane After completion of the dropwise addition, the reaction was stopped and the reaction solution was successively washed with 5% HCl 30 ml * 3, 5% NaOH 30 ml * 3, water 30 ml * 3, saturated Washed with 30 ml of brine, dried over anhydrous magnesium sulfate, filtered, the solvent was distilled off from the filtrate,6.43 g of 2-chloro-N-(3-methoxyphenyl)acetamide are obtained. Yield is 80.7%.

75.2%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.333333h;	General procedure: In a round bottom flask, 10mmol aniline derivitives (4a-n) and 20mmol potassium carbonate were suspended in 15mL DMF and cooled to 0C. Then 12mmol chloroacethylchloride was added. The reaction mixture was then stirred at room temperature for 20min; quenched with saturated sodium hydrogen carbonate (10mL) and washed with water. The organic layer was separated and dried over sodium sulfate. The organic layer was evaporated under reduced pressure, and the crude reaction mixture was purified by column chromatography using chloroform and methanol as a mobile phase to obtain a pure compound [36-39]. The CAS-numbers and yield of synthesized compounds were reported in the supplementary file (Table S1).
75.8%	With triethylamine; In dichloromethane; at 0℃; for 4h;	General procedure: Weigh 0.51g (5mmol) of aniline (5mmol) and triethylamine in a 50mL round bottom flask, add 10mL of dichloromethane, use nitrogen protection, add 0.56g (5mmol) of chloroacetyl chloride, and place in an ice-water bath at 0 and stir. After reacting for 4 hours, add 20mL of dichloromethane to dilute the reaction, wash with 1M hydrochloric acid, saturated sodium bicarbonate solution and brine successively, and use rotary evaporation to remove dichloromethane to obtain substituted aniline (7)
70%		General procedure: To a solution of substituted aniline (compounds 1a-1t) or 5-aminoindole and 6-aminoquinoline (1.0 equiv.) in dichloromethane (CH2Cl2) (15mL) at 0C, potassium carbonate (K2CO3) (2.0 equiv.) was added. The reaction was stirred at 0C for 15min. Into this stirring solution, chloroacetyl chloride (1.0 equiv.) was added dropwise at 0C. The mixture was stirred for 2hat room temperature. After completion of the reaction, water (20mL) was added, and the mixture was extracted with dichloromethane. The organic solvent phase was concentrated under vacuum to afford the desired compounds 2a-2t, 5a and 5b.
53.01%		General procedure: Step 1. To the stirred solution of Aniline (1.0 equiv) in acetone was added K2CO3 (1.2 equiv.) at RT and stirred for 30min. Chloroacetyl chloride/substituted acetylchloride (1.1 equiv.) was then added at 0C and stirred for additional 3h at room temperature. After completion of the reaction (monitored by TLC), volatiles were removed on rotary evaporator and ethyl acetate was added. Organic layer were washed with water, aq NaHCO3, brine. Organic layer was dried over sodium sulfate and evaporated on rotary evaporator and the crude residue was purified by flash chromatography to give the desired product.
	With pyridine; In water; at 0℃; for 1h;	General procedure: Generalprocedure: To a solution of aniline or benzylamine (10 mmol) inwater (20 ml) and pyridine (1.6 ml) was added chloracetyl chloride(1.69 g, 15 mmol) slowly at 0 C. The reaction mixture was stirredat 0 C for 1.0 h and then diluted with water (50 ml). The precipitatewas collected by filtration, washed with water and dried undervacuum. N-substituted-2-chloroacetamides 3a-3r were obtainedas solid (yield 50-80%).
	In N,N-dimethyl-formamide; at 20℃; for 0.333333h;	General procedure: To a stirred solution of substituted aniline (1 mmol) and chloroacetyl chloride (1 mmol) which was stirred in 5 mL DMF for 20 min, were added benzyl amine derivatives (1.3 mmol) and CS2 (5 mmol). The reaction mixture was allowed to stir for required additional time (Table 2). Then, 5 mL of water was added and the solution was extracted with ethyl acetate and dried over sodium sulfate and purified by passing over a silica gel column chromatography using petroleum ether/ethyl acetate (8:2).
	With triethylamine; In dichloromethane; at 20℃; for 0.5h;	General procedure: To a solution of the appropriate amine (50 mmol) in triethylamine (5.1 mg, 50.5 mmol) and dichloromethane (50 mL), chloroacetyl chloride (70 mmol) was added dropwise, and the mixture was allowed to stir at room temperature for 30 min. Then, it was slowly poured into a saturated solution of NaHCO3 (100 mL). The layers were separated, and the aqueous layer was extracted with CH2-Cl2 (30 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The product was dried and recrystallized from ethyl acetate andpetroleum ether to obtain 2-chloro-N-substituted acetamides. The properties and analytical data for these compounds 15a-v were listed in the supporting information.
		General procedure: Under nitrogen atmosphere, dry CH2Cl2 (30 mL), amine (0.02 mol), and Et3N (0.05 mol) wereadded to a three-necked round bottom ask and stirred for 0.5 h, then chloroacetyl chloride droppedslowly and reacted for 3 h at room temperature. Then, the solution was washed with 2 mol L1hydrochloric acid (30 mL), saturated aq NaHCO3 solution (30 mL), and brine (40 mL), successively,then dried over anhydrous Na2SO4 and filtered. After evaporating CH2Cl2 in vacuum, the obtainedcrude product was rened by recrystallization using ethyl acetate/petroleum ether.
	In N,N-dimethyl-formamide; at 20℃; for 0.5h;	General procedure: Mixture of amines 6 and chloroacetyl chloride 7 in DMF werestirred at room temperature for 30 min. At the end of the reaction(checked by TLC), the reaction mixture was diluted with water, pouredinto ice, and the obtained white precipitate was filtered off. The residuewas washed with water to obtain pure N-phenyl (or benzyl)-2-chloroacetamide8.
	With triethylamine; In dichloromethane; at 0 - 25℃; for 20h;	General procedure: 2-Chloroacetyl chloride (24 mmol) wasslowly added dropwise to a mixture of various anilines(20 mmol) and Et3N (24 mmol) in anhydrous CH2Cl2(20 mL) at 0 C. The reaction mixture was warmed to roomtemperature and stirred for an additional 20 h. After the solventwas removed under reduced pressure, the residue waswashed with ice water, and the precipitate was separatedby filtration. The crude product was purified by crystallizationusing a mixture of ether/hexane (2a-r).
	In acetic acid; at 0 - 20℃;	General procedure: Various substituted anilines were dissolved in glacial acetic acidat 0 C, to this was added over 30 min choloroacetylchloride (2equivalents). The reaction mixture was brought to room temperatureand stirred overnight. Saturated sodium bicarbonate solutionwas added till complete neutralization. The resulting precipitatewas filtered off and washed with n-hexane and dried. The resultantproduct was used further without any purification. Either of 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde, vanillin or isovanillin(1 equivalent) was dissolved in acetone and potassiumcarbonate (2 equivalents) was added. Then correspondingsubstituted acetamide was mixed to the stirring solution. Finally,potassium iodide (1.5 equivalent) was added. The reaction mixturewas refluxed for 8-10 h. After completion of reaction, the resultantmixture was concentrated and treated with water and extractedwith ethyl acetate (3 x 20 mL). The organic layers were combinedand treated with brine and dried over sodium sulfate andconcentrated. The crude mixture was purified over silica gel(60-120) using petroleum ether: ethyl acetate (9:1).
	With acetic acid; at 0 - 20℃;	General procedure: Various substituted anilines were dissolved in glacial acetic acid at0 C, to this was added over 30 min choloroacetyl chloride (2 equivalents).The reaction mixture was brought to room temperature andstirred overnight. Saturated sodium bicarbonate solution was added tillcomplete neutralization. The resulting precipitate was filtered off andwashed with n-hexane and dried. The resultant product (1) was usedfurther without any purification. Either of 4-hydroxy benzaldehyde(2a), vanillin (2b) or isovanillin (2c) (1 equivalent) was dissolved inacetone and potassium carbonate (2 equivalents) was added. Thencorresponding substituted acetamide (1) was mixed to the stirring solution.Finally, potassium iodide (1.5 equivalent) was added. The reactionmixture was refluxed for 8-10 h. After completion of reaction,the resultant mixture was concentrated and treated with water andextracted with ethyl acetate (3×20 mL). The organic layers werecombined and treated with brine and dried over sodium sulfate andconcentrated. The crude mixture was purified over silica gel (60-120)using petroleum ether: ethyl acetate (9:1).
	With triethylamine; at 0 - 20℃; for 4h;	General procedure: In a round bottom flask, primary or secondary amines (0.1 mol) and triethyl amine weredissolved in DCM and stirred at 0 C. 2-Chloroacetyl chloride (0.1 mol) was added to reaction mixture drop wise with continuous stirring on magnetic stirrer. After the addition,the ice bath was removed and the reaction mixture was stirred at room temperature for 4 h.The progress of the reaction was monitored by TLC using ethyl acetate: hexane (1:9) as asolvent system. After completion of the reaction, the reaction mixture was poured on crushedice and neutralised by adding acetic acid to it. The obtained solid intermediates of respectiveamines were filtered, dried and crystallised in ethanol.
	With triethylamine; In dichloromethane; at 0 - 20℃; for 12h;	General procedure: A stirred solution of aniline derivatives 1a-h (0.05 mol) in dichloromethane DCM (50 mL) was cooled to 0 C, and chloroacetyl chloride (0.06 mol) and triethylamine (0.06 mol) was added dropwise to the solution. The resulting mixture was warmed to room temperature and stirred overnight. The organic phase was diluted with DCM (50 mL) and washed with 0.5 M HCl (50 mL), then saturated with NaHCO3 and brine. The organic layer was collected and dried over anhydrous Na2SO4. Then, the solvent was removed under reduced pressure. The 2-chloro-N-phenylancetamide derivatives (5 mmol) obtained by recrystallization were refluxed with potassium iodide (7.5 mmol) in acetone (10 mL) for 6 h, and the solvent was evaporated in vacuo. Water (50 mL) was added to the reaction mixture, and the organic phase extracted with ethyl acetate was washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated, then recrystallized from ethyl acetate to obtain Compounds 2a-h [1-3]. Moxifloxacin (2 mmol) and TEA (4.4 mmol) were added to a stirred solution of 2-iodo-N-phenylancetamide derivatives 2a-h (2.2 mmol) in acetonitrile (10 mL). The mixture was heated under reflux for 12 h, then the solvent was removed under vacuum. The resulting solid was recrystallized using acetonitrile to afford eight 4a-h [4].
	With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere;	General procedure: The corresponding amine was dissolved in anhydrous dichloromethane at 0C, and then triethylamine (1.1 eq) was added under a nitrogen atmosphere. Chloroacetyl chloride (1.1 eq) diluted with anhydrous dichloromethane was slowly added to the reaction mixture in an ice bath. The reaction stirred at 0C for 30min, after which the reaction slowly warmed to room temperature overnight. TLC was used to monitor the reaction. After the reaction was complete, it was quenched with water and extracted with dichloromethane. The organic phase was retained and washed with an aqueous hydrochloric acid solution, an aqueous saturated sodium hydrogen carbonate solution, and brine three times. Anhydrous sodium sulfate was used to dry the organic phase, after which the solvent was removed under reduced pressure with a rotary evaporator to obtain crude product. The crude product was dissolved in ethyl acetate and recrystalized with petroleum ether to afford the final product. Compounds 5-14 were in 58-86% yield.

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3
[ 17641-08-6 ]
[ 109-89-7 ]
[ 40517-65-5 ]

References: [1]Journal of the Indian Chemical Society,1940,vol. 17,p. 400,401.

4
[ 17641-08-6 ]
[ 31523-22-5 ]
N-(3-Methoxy-phenyl)-2-[N'-(5H-[1,2,4]triazino[5,6-b]indol-3-yl)-hydrazino]-acetamide [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1989,vol. 66,p. 246 - 247.

5
[ 17641-08-6 ]
[ 64-17-5 ]
[ 77775-78-1 ]
[ 77775-79-2 ]
[ 588-16-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 128 - 136.

6
[ 17641-08-6 ]
[ 17641-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium iodide; In acetone; for 6h;Reflux;	General procedure: A stirred solution of aniline derivatives 1a-h (0.05 mol) in dichloromethane DCM (50 mL) was cooled to 0 C, and chloroacetyl chloride (0.06 mol) and triethylamine (0.06 mol) was added dropwise to the solution. The resulting mixture was warmed to room temperature and stirred overnight. The organic phase was diluted with DCM (50 mL) and washed with 0.5 M HCl (50 mL), then saturated with NaHCO3 and brine. The organic layer was collected and dried over anhydrous Na2SO4. Then, the solvent was removed under reduced pressure. The 2-chloro-N-phenylancetamide derivatives (5 mmol) obtained by recrystallization were refluxed with potassium iodide (7.5 mmol) in acetone (10 mL) for 6 h, and the solvent was evaporated in vacuo. Water (50 mL) was added to the reaction mixture, and the organic phase extracted with ethyl acetate was washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated, then recrystallized from ethyl acetate to obtain Compounds 2a-h [1-3]. Moxifloxacin (2 mmol) and TEA (4.4 mmol) were added to a stirred solution of 2-iodo-N-phenylancetamide derivatives 2a-h (2.2 mmol) in acetonitrile (10 mL). The mixture was heated under reflux for 12 h, then the solvent was removed under vacuum. The resulting solid was recrystallized using acetonitrile to afford eight 4a-h [4].

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 2720 - 2733.
[2]Tetrahedron Letters,2020,vol. 61.

7
[ 17641-08-6 ]
[ 77775-78-1 ]
[ 77775-79-2 ]
[ 588-16-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 128 - 136.

8
[ 17641-08-6 ]
[ 491-36-1 ]
[ 108086-41-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 438 - 440.

9
[ 17641-08-6 ]
[ 147-93-3 ]
[ 97457-48-2 ]

References: [1]European Journal of Medicinal Chemistry,1985,vol. 20,p. 187 - 189.

10
[ 17641-08-6 ]
[ 134469-07-1 ]
[ 83408-89-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 379 - 380.

11
[ 17641-08-6 ]
[ 37893-08-6 ]
[ 132659-09-7 ]

References: [1]Journal of the Indian Chemical Society,1990,vol. 67,p. 485 - 486.

12
[ 17641-08-6 ]
[ 1904-60-5 ]
N-(3-Methoxy-phenyl)-2-(4-oxo-2-phenyl-4H-quinazolin-3-ylamino)-acetamide [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 201 - 208.

13
[ 17641-08-6 ]
[ 23269-70-7 ]
2-[5-(4-Acetylamino-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-N-(3-methoxy-phenyl)-acetamide [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1998,vol. 37,p. 180 - 182.

14
[ 17641-08-6 ]
[ 141-43-5 ]
2-(2-Hydroxy-ethylamino)-N-(3-methoxy-phenyl)-acetamide [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 7459 - 7462.

15
[ 17641-08-6 ]
[ 873-55-2 ]
2-benzenesulfonyl-N-(3-methoxy-phenyl)-acetamide [ No CAS ]

References: [1]Magnetic Resonance in Chemistry,2000,vol. 38,p. 384 - 385.

Yield	Reaction Conditions	Operation in experiment
63.8%	With pyridine; In water; at 0℃; for 1h;Cooling with ice;	General procedure: The 1.27g (10mmol, 1 . 0eq) 4-aminochlorobenzene into 1.6 ml pyridine with 20 ml of water in the mixed solution, under the condition in the ice bath, dripping therein 1.69g (15mmol, 1 . 5eq) chloro acetyl chloride. In 0 C reaction 1.0h, in to the system by adding 50 ml of water, filtering, filtering the solid obtained after drying 0.77g white powdery solid, can be without purification directly used for the next reaction, the yield is 37.7%

17
[ 17641-08-6 ]
[ 74331-44-5 ]
N-(3-methoxy-phenyl)-2-(2-oxo-1,3-diphenyl-2,3-dihydro-1H-imidazol-4-ylsulfanyl)-acetamide [ No CAS ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,2001,vol. 170,p. 47 - 63.

18
[ 17641-08-6 ]
[ 74331-44-5 ]
6-(3-methoxy-phenylamino)-1,3-diphenyl-1,3-dihydro-thieno[2,3-d]imidazol-2-one [ No CAS ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,2001,vol. 170,p. 47 - 63.

19
[ 17641-08-6 ]
5-chloro benzoxazole 2-thiol potassium salt [ No CAS ]
2-(5-chloro-benzooxazol-2-ylsulfanyl)-N-(3-methoxy-phenyl)-acetamide [ No CAS ]

References: [1]Pakistan Journal of Scientific and Industrial Research,2002,vol. 45,p. 219 - 225.

20
[ 17641-08-6 ]
[ 56278-50-3 ]
5-amino-4-(2-benzothiazolyl)-2,3-dihydro-1-(3-methoxyphenyl)-2-pyrrolone [ No CAS ]

References: [1]Synthesis,2002,p. 2717 - 2724.

21
[ 17641-08-6 ]
[ 610278-84-7 ]
4-(5-amino-4-benzothiazol-2-yl-3-oxo-2,3-dihydro-pyrrol-1-yl)-benzoic acid (3-methoxy-phenylcarbamoyl)-methyl ester [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2004,vol. 40,p. 368 - 371.

22
[ 17641-08-6 ]
[ 749216-03-3 ]
3-{5-amino-4-[4-(4-chloro-phenyl)-thiazol-2-yl]-3-oxo-2,3-dihydro-pyrrol-1-yl}-benzoic acid (3-methoxy-phenylcarbamoyl)-methyl ester [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2004,vol. 40,p. 368 - 371.

23
[ 17641-08-6 ]
[ 84951-44-0 ]
2-[4-(3-cyano-pyridin-2-yl)-piperazin-1-yl]-N-(3-methoxy-phenyl)-acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3471 - 3483.

24
[ 17641-08-6 ]
[ 17969-48-1 ]
5-amino-4-[4-(4-chloro-phenyl)-thiazol-2-yl]-1-(3-methoxy-phenyl)-1,3-dihydro-pyrrol-2-one [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 257 - 260.

25
[ 870537-61-4 ]
[ 17641-08-6 ]
N-(3-Methoxy-phenyl)-2-(5-{4-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-phenyl}-[1,3,4]oxadiazol-2-ylsulfanyl)-acetamide [ No CAS ]

References: [1]Journal of the Indian Chemical Society,2005,vol. 82,p. 746 - 747.

26
[ 17641-08-6 ]
[ 122-52-1 ]
[ 803686-21-7 ]

References: [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 2129 - 2139.
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 4332 - 4341.

27
[ 17641-08-6 ]
[ 53-86-1 ]
[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid (3-methoxyphenylcarbamoyl)methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4820 - 4833.

28
[ 17641-08-6 ]
(Z)-3-[7-(1-phenylethoxy)benzofuran-2-yl]-2-butenoic acid (3-methoxyphenyl)amide [ No CAS ]