15308-01-7

Basic information

• Product Name: 2-chloro-N-(2,6-dichlorophenyl)-N-phenylacetamide
• Synonyms: N-Chloro Acetyl-2,6 Dichloro Diphenyl Amine;N-(2,6-DICHLOROPHENYLACETANILIDE;2,2',6'-Trichloro-N-phenylacetanilide;N-(2,6-Dichlorophenyl)-N-phenylchloroacetamide;N-(2,6-Dichlorophenyl)-α-chloroacetanilide;Einecs 239-350-6;Diclofenac Related Compound (N-Chloroacetyl-N-phenyl-2,6-dichloroaniline);Diclofenac Chloroacetyl Impurity
• CAS NO: 15308-01-7
• Molecular Formula: C₁₄H₁₀Cl₃NO
• Molecular Weight: 314.5943
• EINECS: 239-350-6
• Mol File: 15308-01-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 143-144 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 487.5 °C at 760 mmHg
• Flash Point: 248.6 °C
• Appearance: White to off white crystalline powder
• Density: 1.411 g/cm³
• Vapor Pressure: 1.18E-09mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -5.47±0.50(Predicted)
• CAS DataBase Reference: 2-chloro-N-(2,6-dichlorophenyl)-N-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-N-(2,6-dichlorophenyl)-N-phenylacetamide(15308-01-7)
• EPA Substance Registry System: 2-chloro-N-(2,6-dichlorophenyl)-N-phenylacetamide(15308-01-7)

Safety Data

• Hazardous Substances Data: 15308-01-7(Hazardous Substances Data)

Usage

Uses

2-Chloro-N-(2,6-dichlorophenyl)-N-phenylacetamide is used as a reactant in the preparation of 1-(2,6-dichlorophenyl)-3-methylene-1,3-dihydro-indol-2-one derivatives with in vitro cytotoxic activity on SW620 colon cancer cell lines.

InChI:InChI=1/C14H10Cl3NO/c15-9-13(19)18(10-5-2-1-3-6-10)14-11(16)7-4-8-12(14)17/h1-8H,9H2

Synthetic route

N-phenyl-2,6-dichloroaniline (15307-93-4) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7)

Conditions	Yield
at 106 - 110℃; for 2h; Acetylation;	86%
for 16h; Heating;	66%
for 5h; Reflux;
for 5h; Reflux;
In toluene at 120℃; for 3h; Solvent;

2,2,6,6-tetrachlorocyclohexanone (3776-30-5) → 2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / TiCl4 / toluene / 2 h / 20 °C 2: Et3N / dimethylformamide / 5 h / 95 - 100 °C 3: 86 percent / 2 h / 106 - 110 °C View Scheme

aniline (62-53-3) + Wang resin-bound styrene 4 → 2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / TiCl4 / toluene / 2 h / 20 °C 2: Et3N / dimethylformamide / 5 h / 95 - 100 °C 3: 86 percent / 2 h / 106 - 110 °C View Scheme

N-phenyl-2,2,6,6-tetrachlorocyclohexaneimine (123066-65-9) → 2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / dimethylformamide / 5 h / 95 - 100 °C 2: 86 percent / 2 h / 106 - 110 °C View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
With aluminium trichloride at 160℃; for 2h;	75.4%
With aluminum (III) chloride at 160℃; for 2h;	62%
With aluminum (III) chloride at 160℃; for 2h;
With triethylamine hydrochloride-aluminum trichloride at 20 - 60℃; for 4.5h; Reagent/catalyst;

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → diclofenac sodium (15307-79-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75.4 percent / AlCl3 / 2 h / 160 °C 2: 93 percent / 2 N NaOH / ethanol; H2O / 4 h / Heating View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(4-chlorophenyl)]methylene}-1,3-dihydroindol-2-one (1146981-11-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(4-fluorophenyl)]methylene}-1,3-dihydroindol-2-one (1146981-16-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(4-hydroxyphenyl)]methylene}-1,3-dihydroindol-2-one (1146981-19-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(4-(dimethylamino)phenyl)]methylene}-1,3-dihydroindol-2-one (145253-61-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(3-chlorophenyl)]methylene}-1,3-dihydroindol-2-one (1146981-10-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-(2,6-dichlorophenyl)-3-(3-bromobenzylidene)-1,3-dihydroindol-2-one (1146981-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(3-phenoxyphenyl)]methylene}-1,3-dihydroindol-2-one (1146981-18-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-(2,6-dichlorophenyl)-3-((2,6-dichlorophenyl)methylene)-1,3-dihydroindol-2-one (1146981-13-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(2-chloroquinolin-3-yl)]methylene}-1,3-dihydroindol-2-one (1146981-23-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(2-chloro-6-methylquinolin-3-yl)]methylene}-1,3-dihydroindol-2-one (1146981-24-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → C26H17Cl3N2O (1146981-25-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(furan-2-yl)]methylene}-1,3-dihydro-indol-2-one (1146981-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-(2,6-dichlorophenyl)-3-((phenyl)methylene)-1,3-dihydroindol-2-one (15307-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(2-chlorophenyl)]methylene}-1,3-dihydroindol-2-one (1146981-09-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(2-nitrophenyl)]methylene}-1,3-dihydroindol-2-one (1146981-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(3,4-dimethoxyphenyl)]methylene}-1,3-dihydroindol-2-one (1146981-20-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-{[(2,6-dichlorophenyl)-3-(naphthalen-1-yl)]methylene}-1,3-dihydroindol-2-one (1146981-21-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 2 h / 160 °C 2: piperidine / ethanol / Reflux; Inert atmosphere View Scheme

Upstream product

• 587-65-5 N-chloroacetyl-aniline 
• 62-53-3 aniline 
• 3776-30-5 2,2,6,6-tetrachlorocyclohexanone 
• 15307-93-4 N-phenyl-2,6-dichloroaniline 
• 79-04-9 chloroacetyl chloride 
• 123066-65-9 N-phenyl-2,2,6,6-tetrachlorocyclohexaneimine 

Downstream Products

• 1146981-21-6 1-{[(2,6-dichlorophenyl)-3-(naphthalen-1-yl)]methylene}-1,3-dihydroindol-2-one 
• 1146981-20-5 1-{[(2,6-dichlorophenyl)-3-(3,4-dimethoxyphenyl)]methylene}-1,3-dihydroindol-2-one 
• 1146981-15-8 1-{[(2,6-dichlorophenyl)-3-(2-nitrophenyl)]methylene}-1,3-dihydroindol-2-one 
• 1146981-09-0 1-{[(2,6-dichlorophenyl)-3-(2-chlorophenyl)]methylene}-1,3-dihydroindol-2-one 
• 15307-68-3 1-(2,6-dichlorophenyl)-3-((phenyl)methylene)-1,3-dihydroindol-2-one 
• 1146981-22-7 1-{[(2,6-dichlorophenyl)-3-(furan-2-yl)]methylene}-1,3-dihydro-indol-2-one 
• 1146981-25-0 C₂₆H₁₇Cl₃N₂O 
• 1146981-24-9 1-{[(2,6-dichlorophenyl)-3-(2-chloro-6-methylquinolin-3-yl)]methylene}-1,3-dihydroindol-2-one 
• 1146981-23-8 1-{[(2,6-dichlorophenyl)-3-(2-chloroquinolin-3-yl)]methylene}-1,3-dihydroindol-2-one 
• 1146981-13-6 1-(2,6-dichlorophenyl)-3-((2,6-dichlorophenyl)methylene)-1,3-dihydroindol-2-one 
• 1146981-18-1 1-{[(2,6-dichlorophenyl)-3-(3-phenoxyphenyl)]methylene}-1,3-dihydroindol-2-one 
• 1146981-17-0 1-(2,6-dichlorophenyl)-3-(3-bromobenzylidene)-1,3-dihydroindol-2-one 
• 1146981-10-3 1-{[(2,6-dichlorophenyl)-3-(3-chlorophenyl)]methylene}-1,3-dihydroindol-2-one 
• 145253-61-8 1-{[(2,6-dichlorophenyl)-3-(4-(dimethylamino)phenyl)]methylene}-1,3-dihydroindol-2-one 

Relevant articles and documents

Synthesis method of diclofenac sodium

The invention discloses a synthesis method of diclofenac sodium, which comprises the following steps: (1) toluene. An oil layer is obtained by adding 2, 6 -dichlorophenol and sodium carbonate, keeping warm and refluxing, extracting the oil layer with water, and adding an alkali heat-preserving reaction in the oil layer to obtain 2, 6 -dichloroaniline. (2) 1, 2 Dichlorodimethylaniline prepared in step (6 -) is heated and melted, chloroacetyl chloride is added dropwise, and the heat is subjected to heat preservation reaction after being heated to crystallize to obtain N - (2, 6 - dichlorophenyl) - phenyl - chloroacetamide. (3) 2 (N - 2 Dichlorophenyl) 6 - phenyl - chloroacetamide prepared in step (-) is reacted with the aluminum trichloride to give a solid 1 - (2, 6 -dichlorophenyl) -2 -indolinone. (4) 3 (1 - 2-dichlorophenyl) 6 -indolinone prepared in step (-2 -) is added to alkali liquor, stirred and heated to reflux to obtain diclofenac sodium. The synthesis method is stable, easy to operate, low in cost, high in yield and suitable for industrial production.

In vitro cytotoxicity evaluation of diversely substituted N-aryl-2-oxindoles

In continuation with our previous work, structurally diverse 2-indolinones bearing 2,6-dichloroaryl fragment at N 1 and (hetero)aryl benzylidene at C3 were evaluated for their antitumor activity on a panel of cancer cell lines such as MCF-7 (breast), MiapaCa2 (pancreas), KB (oral), HuTu80 (stomach), L132 (lung), B16F10 (melanoma), and Molt4 (leukemia) from various human organs. Among the screened compound library, molecules 4e, 4k, and 4r have shown excellent cytotoxicity on a stomach cancer cell line. Moreover, a significant number of compounds have also shown promising cytotoxicity on pancreas and oral cancer cell lines.

An advanced method for the preparation of 2,6-dichlorodiphenylamine and its N-chloroacetyl derivative - Intermediates in the synthesis of antiinflammatory drug ortophenum

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