2,6-Dichlorodiphenylamine | Aryls

2,6-Dichlorodiphenylamine is an analogue of Diclofenac Sodium and has anti-Candida albicans activity. Diclofenac Sodium is a potent and nonselective anti-inflammatory agent, acts as a COX inhibitor, with IC50s of 4 and 1.3 nM for human COX-1 and COX-2 in CHO cells.

Synonyms: 2,6-Dichloro-N-phenylaniline

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Quality Control of 2,6-Dichlorodiphenylamine Purity: 99% SDS Specification

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Product Details of 2,6-Dichlorodiphenylamine

CAS No. :	15307-93-4
Formula :	C₁₂H₉Cl₂N
M.W :	238.11
SMILES Code :	ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1
Synonyms :	2,6-Dichloro-N-phenylaniline
MDL No. :	MFCD00269648

Safety of 2,6-Dichlorodiphenylamine

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 2,6-Dichlorodiphenylamine

* 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 [ 15307-93-4 ]

[ 15307-93-4 ] Synthesis Path-Downstream 1~35

1
[ 79-37-8 ]
[ 15307-93-4 ]
[ 24542-55-0 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2358 - 2368.

2
[ 35928-65-5 ]
[ 15307-93-4 ]
[ 83281-93-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.

3
[ 15307-93-4 ]
[ 79-04-9 ]
[ 15308-01-7 ]

References: [1]Pharmaceutical Chemistry Journal,1996,vol. 30,p. 38 - 40.
[2]Journal of Medicinal Chemistry,1990,vol. 33,p. 2358 - 2368.
[3]European Journal of Medicinal Chemistry,2009,vol. 44,p. 1355 - 1362.
[4]Medicinal Chemistry Research,2013,vol. 22,p. 3076 - 3084.

4
[ 15307-93-4 ]
(1S,2S)-2-(2,2-Dichloro-vinyl)-1,2,3,3-tetramethyl-cyclopropanecarbonyl chloride [ No CAS ]
[4-(2,6-Dichloro-phenylamino)-phenyl]-[(1S,2S)-2-(2,2-dichloro-vinyl)-1,2,3,3-tetramethyl-cyclopropyl]-methanone [ No CAS ]

References: [1]Synthetic Communications,1998,vol. 28,p. 2203 - 2206.

5
[ 15307-93-4 ]
[ 3282-30-2 ]
1-[4-(2,6-dichloro-phenylamino)-phenyl]-2,2-dimethyl-propan-1-one [ No CAS ]

References: [1]Synthetic Communications,1998,vol. 28,p. 2203 - 2206.

6
[ 15307-93-4 ]
[ 122-01-0 ]
(4-chloro-phenyl)-[4-(2,6-dichloro-phenylamino)-phenyl]-methanone [ No CAS ]

References: [1]Synthetic Communications,1998,vol. 28,p. 2203 - 2206.

7
[ 123066-65-9 ]
[ 15307-93-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydroxide; In chlorobenzene;	EXAMPLE 22 A 1 l glass reactor was charged with 100 g (0.32 mole) of N-phenyl-2,2,6,6-tetrachlorocyclohexaneimine obtained in Example 1 and 500 g of chlorobenzene, and the mixture was heated in an oil bath with stirring. While keeping the reaction temperature at 100 C., the reaction was continued for 5 hours. After the reaction was completed, the reaction mixture was cooled to 25 C., and washed with 300 g of a 10% aqueous solution of sodium hydroxide. Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure to give 64.7 g of N-phenyl-2,6-dichloroaniline in the state of a black solid (yield: 85%, mp: 49.5 to 50.7 C.). The obtained N-phenyl-2,6-dichloroaniline had a purity of 92.1% measured by means of gas chromatography. After N-phenyl-2,6-dichloroaniline was purified by recrystallizing from methanol, 1 H-NMR analysis, IR analysis and elementary analysis were conducted. The results are shown below. 1 H-NMR (solvent: CDCl3, internal standard: TMS): delta ppm: 7.53 to 6.55 (8H, m, benzene ring), 5.83 (1H, S, NH). IR (KBr tablet): nu NH: 3380 (cm-1).

References: [1]Patent: US4908479,1990,A .
[2]Pharmaceutical Chemistry Journal,1996,vol. 30,p. 38 - 40.

8
[ 15307-93-4 ]
[ 112-67-4 ]
1-[4-(2,6-dichloro-phenylamino)-phenyl]-hexadecan-1-one [ No CAS ]

References: [1]Synthetic Communications,1998,vol. 28,p. 2203 - 2206.

Yield	Reaction Conditions	Operation in experiment
87%		EXAMPLE 23 The procedure of Example 22 was repeated except that 40 g (0.38 mole) of sodium carbonate was used and that the reaction temperature was kept at 95° C. to give 66.3 g of N-phenyl-2,6-dichloroaniline (yield: 87percent, purity: 95.1percent).
		EXAMPLE 2 Preparation of 2,6-dichlorodiphenylamine A mixture of 996 g of 2,6-dichlorophenoxyacetic acid ethyl ester, 500 ml of aniline and 400 ml of n-butanol is preheated to 100° C. in a distillation apparatus. 400 ml of 5.5N sodium methylate are run in over a period of 30 minutes during which a flow of distillate is maintained by the exothermic heat of the reaction. After addition of the sodium methylate, stirring is continued for 15 minutes at 100° C. with continued removal of distillate. 1 l of water is then added and solvent is distilled off down to the sump temperature of 90° C. Phase separation takes place at 60° C. The solvent is drawn off in a vacuum and the product is crystallized from 1l of 90percent i-propanol. The product is separated by suction filtration at 0° C. and washed with dilute i-propanol. Yield: 727 g=76.5percent of the theoretical yield with exploitation of the mother liquor to an extent of 82percent of the theoretical.

10
[ 19393-92-1 ]
[ 62-53-3 ]
[ 15307-93-4 ]

References: [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 23 - 39.

11
[ 108-86-1 ]
[ 608-31-1 ]
[ 15307-93-4 ]

References: [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 23 - 39.

12
[ 3776-30-5 ]
[ 15307-93-4 ]

References: [1]Pharmaceutical Chemistry Journal,1996,vol. 30,p. 38 - 40.

13
[ 62-53-3 ]
Wang resin-bound styrene 4 [ No CAS ]
[ 15307-93-4 ]

References: [1]Pharmaceutical Chemistry Journal,1996,vol. 30,p. 38 - 40.

14
[ 15307-93-4 ]
[ 15362-40-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.
[2]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.
[3]Journal of Medicinal Chemistry,1990,vol. 33,p. 2358 - 2368.
[4]Medicinal Chemistry Research,2013,vol. 22,p. 3076 - 3084.

15
[ 15307-93-4 ]
[ 15307-86-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.
[2]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.

16
[ 15307-93-4 ]
[ 15307-79-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.
[2]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.
[3]Journal of Medicinal Chemistry,1990,vol. 33,p. 2358 - 2368.
[4]Journal of Medicinal Chemistry,1990,vol. 33,p. 2358 - 2368.

17
[ 15307-93-4 ]
[ 83281-94-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.
[2]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.

18
[ 15307-93-4 ]
[ 83281-96-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.

19
[ 15307-93-4 ]
α-chloro-N-(2,6-dichlorophenyl)-α-(methylthio)acetanilide [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.

20
[ 15307-93-4 ]
[ 83281-95-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.
[2]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1995 - 1997.

21
[ 15307-93-4 ]
[ 24542-74-3 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2358 - 2368.

22
[ 15307-93-4 ]
[ 66156-75-0 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2358 - 2368.

23
HC₁₀₄ [ No CAS ]
[ 112905-76-7 ]
[ 15307-93-4 ]
[ 7732-18-5 ]
[ 149299-43-4 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; hexane; diethylene glycol dimethyl ether; acetone;	e. N-(2,6-dichlorophenyl)-beta-[[(1-methylcyclohexyl) -methoxy]methyl]-N-phenyl-1-pyrrolidineethanamine perchlorate (1:1) A 250 ml, 3-necked, round bottom flask was equipped with a magnetic stirrer, addition funnel, argon inlet and outlet and a silicone oil bath. Sodium hydride (60percent, 2.19 g, 1.2 eq) was added to the reaction vessel and extracted twice with Et2 O under argon. Diglyme (50 ml) was then added followed by potassium hydride (50 mg). The slurry was heated to 110° C. under argon with stirring. To the addition funnel was then added <strong>[15307-93-4]N-phenyl-2,6-dichloroaniline</strong> (11.21 g, 0.0456 m) (the product of Example 1d.) and 1-[2-chloro-3-(1-methylcyclohexyl)methoxypropyl]pyrrolidine (15 g, 0.0548 m) (the product of Example 1c) which was diluted with 20 ml of diglyme. The mixture was added dropwise over 15 min, allowing for the smooth evolution of hydrogen gas. The reaction is slightly exothermic. After 15 min, the reaction mixture was cooled to RT, quenched with 20 ml of H2 O and concentrated on a rotary evaporator. The orange residue was partitioned between H2 O and CH2 Cl2. The H2 O layer was extracted twice with CH2 Cl2 and the combined CH2 Cl2 extracts were washed with H2 O, brine, dried over anhydrous K 2 CO3, filtered through diacalite and concentrated under vacuum to give 24.1 g (93percent yield) of the title product as an orange oil. The product was purified on a preparative, high pressure liquid chromatography apparatus using hexane; acetone (92:8) to give 19.56 g of product. The product was dissolved in 75 ml of absolute EtOH and treated with 1.0 eq (3.53 ml of 70percent of HC104) and crystals were allowed to form at RT for 1 hr and in an ice bath for 2 hr. The crystals were filtered and air dried with suction to give 19.29 g of the title product. The product was recrystallized from EtOH, mp 183°-185° C. Elemental Analysis Calculated: C, 56.31; H, 6.48; N, 4.86; Found: C, 56.39; H, 6.48; N, 4.77

References: [1]Patent: US5185362,1993,A .

24
[ 87-65-0 ]
[ 15307-93-4 ]
[ 52839-80-2 ]
[ 172494-87-0 ]

Yield	Reaction Conditions	Operation in experiment
72.7%	With sodium hydroxide; In N,N-dimethyl-formamide; toluene;	EXAMPLE 7 Preparation of 2',6'-dichlorophenyl 2-methylphenyl amine According to method illustrated in the example 1, 2,6-dichlorophenol, toluene and sodium hydroxide were mixed with 45 g of 2-methyl-N-phenyl chloroacetamide and N,N-dimethylformamide, then refluxed in an oil bath. The toluene recovered from the reflux was mixed and reacted with N,N-dimethylformamide solution prepared in advance. The reacted mixture was washed twice with water. 45 g of 2',6'-dichlorophenyl 2-methylphenyl amine was obtained when the toluene layer was dehydrated with magnesium sulfate, then concentrated. The product yield was 72.7percent.

References: [1]Patent: US5475139,1995,A .

25
[ 87-65-0 ]
[ 527-60-6 ]
[ 7462-76-2 ]
[ 15307-93-4 ]

Yield	Reaction Conditions	Operation in experiment
90.75%	With sodium hydroxide; In water; N,N-dimethyl-formamide; toluene;	EXAMPLE 1 Preparation of N-phenyl 2,6-dichloroaniline 37.6 g of 2,4,6-trimethyl phenol and 11 g of sodium hydroxide were dissolved in 30 ml of water and mixed with 150 ml of toluene. The toluene recovered from heating was mixed with 139 ml of N,N-dimethylformamide to obtain a N,N-dimethylformamide solution. 40 g of 2,6-dichlorophenol was dissolved in 130 ml of toluene, followed by the addition of 9.8 g of sodium hydroxide in 20 ml of water, 41.5 g of N-phenyl chloroacetamide and 8.7 ml of N,N-dimethylformamide, and refluxed in a oil bath at 140°-150° C. for 15 h. The toluene was recovered from the reflux, and mixed with the above N,N-dimethylformamide solution and reacted for 3 h. Recovering N,N-dimethylformamide from the reacted mixture with distillation under reduced pressure (145°-150° C., 8 mm Hg) resulted in the formation of 53 g of N-phenyl 2,6-dichloroaniline and the product yield was 90.75percent.

References: [1]Patent: US5475139,1995,A .

26
[ 7623-09-8 ]
[ 15307-93-4 ]
[ 21694-91-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4026 - 4030.

28
[ 15307-93-4 ]
[ 1146981-11-4 ]