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[ CAS No. 39885-50-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 39885-50-2
Chemical Structure| 39885-50-2
Chemical Structure| 39885-50-2
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Product Details of [ 39885-50-2 ]

CAS No. :39885-50-2 MDL No. :MFCD00042563
Formula : C7H5ClF3N Boiling Point : -
Linear Structure Formula :- InChI Key :MBBUTABXEITVNY-UHFFFAOYSA-N
M.W : 195.57 Pubchem ID :162001
Synonyms :

Calculated chemistry of [ 39885-50-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.86
TPSA : 26.02 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) : -5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 3.06
Log Po/w (WLOGP) : 4.1
Log Po/w (MLOGP) : 3.15
Log Po/w (SILICOS-IT) : 2.77
Consensus Log Po/w : 2.98

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.28
Solubility : 0.102 mg/ml ; 0.00052 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.104 mg/ml ; 0.000533 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.54
Solubility : 0.0558 mg/ml ; 0.000285 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 39885-50-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 39885-50-2 ]

* 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 [ 39885-50-2 ]

[ 39885-50-2 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 39885-50-2 ]
  • [ 27738-96-1 ]
  • [ 35631-27-7 ]
  • [ 39886-31-2 ]
  • 3
  • [ 75-63-8 ]
  • [ 106-47-8 ]
  • [ 433-94-3 ]
  • [ 39885-50-2 ]
  • 4
  • [ 39885-50-2 ]
  • [ 4318-56-3 ]
  • [ 133373-70-3 ]
  • 5
  • [ 75-63-8 ]
  • [ 95-51-2 ]
  • [ 433-94-3 ]
  • [ 39885-50-2 ]
  • [ 88-17-5 ]
  • 6
  • [ 782482-64-8 ]
  • [ 39885-50-2 ]
  • 2-(2-chloro-4-trifluoromethyl-phenylazo)-2,3-dicyano-4-methyl-pentanoic acid ethyl ester [ No CAS ]
  • 7
  • [ 52685-35-5 ]
  • [ 39885-50-2 ]
  • 2-(2-chloro-4-trifluoromethyl-phenylazo)-2,3-dicyano-4,4-dimethyl-pentanoic acid ethyl ester [ No CAS ]
  • 8
  • [ 916065-16-2 ]
  • [ 39885-50-2 ]
  • [ 916065-17-3 ]
YieldReaction ConditionsOperation in experiment
52% With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane;Heating / reflux; Reference Example 10 N-[2-Chloro-4-(trifluoromethyl)phenyl]-7-(2-fluoro-6-methoxyphenyl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine-5-amine 5-Chloro-7-(2-fluoro-6-methoxyphenyl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine(9.06 g)(a compound obtained in Reference Example 9), 2-chloro-4-trifluoromethylaniline(6.22 g), tris(dibenzylidenecetone)dipalladium(0)(0.832 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxantene(1.58 g) and cesium carbonate(14.8 g) were dissolved in 1,4-dioxane(250 mL) under argon atmosphere, the solution was degassed by passing argon gas and it was heated under reflux overnight. After being cooled to room temperature, water(300 mL) and ethyl acetate(300 mL) were added to the solution and the mixture was stirred for five minutes. The separated organic layer was washed with a saturated brine, dried over sodium sulfate and the solvent was evaporated under reduced pressure. The resulting residue was purified by using a silica gel column chromatography (hexane:ethyl acetate=4:1) and the solid product was triturated in ethyl acetate-diethyl ether. The precipitates were collected by filtration to give the titled compound(6.61 g, 52percent yield) as a pale yellow amorphous. MS(APCI)m/z:558/560[M+H]+.
  • 9
  • [ 916065-15-1 ]
  • [ 39885-50-2 ]
  • [ 916065-20-8 ]
YieldReaction ConditionsOperation in experiment
58% With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; for 16h;Heating / reflux; Reference Example 13 7-Benzyloxy-N-[2-chloro-4-(trifluoromethyl)phenyl]-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine-5-amine A mixture of 7-(Benzyloxy)-5-chloro-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine(53.0 g), <strong>[39885-50-2]2-chloro-4-(trifluoromethyl)aniline</strong>(38.1 g), tris(dibenzylideneacetone)dipalladium(0)(5.10 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene(9.66 g)(a compound obtained in Reference Example 12), cesium carbonate(90.7 g) and 1,4-dioxane(1.05 L) was heated under reflux for 16 hours under argon atmosphere. After being cooled to room temperature, ethyl acetate(1 L) was added to the reaction mixture and filtered through Celite. The residue on the Celite was washed with ethyl acetate(1 L) and chloroform(500 mL), the washings were combined with the filtrate, and concentrated under reduced pressure. The resulting residue was crystallized and triturated in ethyl acetate-diethyl ether(1:1) and the crystalline was filtered and washed with ethyl acetate-diethyl ether(1:1). The obtained crystalline was dried to give the titled compound(43.7 g, 58percent yield) as a pale yellow crystalline. mp.189-192°C, MS(APCI)M/z:540/S42[M+H]+.
  • 10
  • [ 916065-28-6 ]
  • [ 39885-50-2 ]
  • [ 916065-29-7 ]
YieldReaction ConditionsOperation in experiment
88% With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane;Heating / reflux; Reference Example 24 N-[2-Chloro-4-(trifluoromethyl)phenyl]-7-(2-fluoro-6-methoxyphenyl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-d]pyrimidine-5-amine 5-Chloro-7-(2-fluoro-6-methoxyphenyl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-d]pyrimidine(1.0 g)(a compound obtained in Reference Example 23), 2-chloro-4-trifluoromethylaniline(982 mg), tris(dibenzylideneacetone)dipalladium(0)(92 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene(0.17 g) and cesium carbonate(1.63 g) were mixed in 1,4-dioxane(28 mL), the reaction vessel was degassed after argon gas was passed through the solution and it was heated under reflux under argon atmosphere overnight. After being cooled to room temperature, water(30 mL) and ethyl acetate(30 mL) were added to the reaction mixture, and it was stirred for 5 minutes. The separated organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by using a silica gel column chromatography(hexane:ethyl acetate=4:1) to give the titled compound(1.24 g, 88percent yield) as a colorless amorphous. MS(APCI)m/z:558/560[M+H]+.
  • 11
  • [ 39885-50-2 ]
  • 5-amino-4-<i>tert</i>-butyl-1-(2-chloro-4-trifluoromethyl-phenyl)-1<i>H</i>-pyrazole-3-carbonitrile [ No CAS ]
  • 12
  • [ 39885-50-2 ]
  • 5-amino-1-(2-chloro-4-trifluoromethyl-phenyl)-4-isopropyl-1<i>H</i>-pyrazole-3-carbonitrile [ No CAS ]
  • 13
  • [ 39885-50-2 ]
  • [ 116687-18-4 ]
  • 14
  • [ 39885-50-2 ]
  • [ 146139-69-7 ]
  • 15
  • [ 39885-50-2 ]
  • N-[2-(2,4-Difluoro-phenoxy)-4-trifluoromethyl-phenyl]-methanesulfonamide [ No CAS ]
  • 16
  • [ 39885-50-2 ]
  • [ 133373-81-6 ]
  • 17
  • [ 39885-50-2 ]
  • [ 121-50-6 ]
  • (2-Cl-4-CF3C6H3NH3)Cl [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; chlorobenzene; at 0℃; for 0.5h; (b) raney Nickel (0.7 g) was added to a solution of the above isomer mixture (35.85 g) in ethanol in a hydrogenation reactor at 50° C. under hydrogen at 5 bar for 5 hours.. The mixture was cooled, filtered and evaporated to give a 95/5 mixture of 2-chloro-4-trifluoromethylaniline and 2-chloro-5-trifluoromethylaniline (33.1 g).. hydrogen chloride gas was added over 0.5 hour to a solution of the above mixture in ethanol and chlorobenzene, cooled to 0° C., and filtered to give 2-chloro-4-trifluoromethylaniline hydrochloride (33.5 g), having a purity of >99percent.. The overall yield from 3,4-dichlorobenzotrifluoride was 85percent.
  • 18
  • [ 374-35-6 ]
  • [ 39885-50-2 ]
  • C11H8ClF6NO2 [ No CAS ]
  • 19
  • [ 1869-22-3 ]
  • [ 86398-98-3 ]
  • [ 39885-50-2 ]
  • [ 121-50-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;nickel; In ethanol; at 50℃; under 3750.38 Torr; for 5h; (b) raney Nickel (0.7 g) was added to a solution of the above isomer mixture (35.85 g) in ethanol in a hydrogenation reactor at 50° C. under hydrogen at 5 bar for 5 hours.. The mixture was cooled, filtered and evaporated to give a 95/5 mixture of 2-chloro-4-trifluoromethylaniline and 2-chloro-5-trifluoromethylaniline (33.1 g).. hydrogen chloride gas was added over 0.5 hour to a solution of the above mixture in ethanol and chlorobenzene, cooled to 0° C., and filtered to give 2-chloro-4-trifluoromethylaniline hydrochloride (33.5 g), having a purity of >99percent.. The overall yield from 3,4-dichlorobenzotrifluoride was 85percent.
  • 20
  • [ 86398-98-3 ]
  • [ 39885-50-2 ]
YieldReaction ConditionsOperation in experiment
100% The procedure of Example 1 was repeated but using 2-chloro-4-trifluoromethylphenylhydrazine, to give the title compound in 100percent yield.
By proceeding in a similar manner there were also prepared with similar results: 2-chloro-4-trifluoromethylaniline; and 2,6-dichloro4-trifluoromethylaniline.
  • 21
  • [ 455-14-1 ]
  • [ 24279-39-8 ]
  • [ 39885-50-2 ]
YieldReaction ConditionsOperation in experiment
98%; 0.09% With chlorine; In chlorobenzene; at 110℃; for 6.5h; 12 140 kg of pure monochlorobenzene are charged to a 20 m3 jacketed reactor rendered inert with nitrogen. The solvent heel is subsequently brought to 110C by heating the jacket. The reactor is subsequently fed with a 70percent solution of para-trifluoromethylaniline in monochlorobenzene at a flow rate of 792 kg/h for 6 h 30 and with Cl at a flow rate of 488 kg/h. The temperature is maintained at 110C by cooling the jacket. Once feeding is complete, the residual content of para-trifluoromethylaniline or of monochloro derivative is monitored. If one of these compounds remains, it is then advisable to adjust the amount of chlorine in order to consume the residual product. At the end of the reaction, the monochlorobenzene is distilled off by placing the reactor under gradually increasing vacuum through a distillation column. After removal of the solvent, the 2,6-dichloro-para-trifluoromethylaniline is cooled to 60C before emptying the reactor to the storage tank.
  • 22
  • [ 140-89-6 ]
  • [ 39885-50-2 ]
  • [ 401567-22-4 ]
YieldReaction ConditionsOperation in experiment
99% A mixture of 2-chloro-4-trifluoromethylaniline (15.0 g, 76.7 mmol) and potassium O-ethyl dithiocarbonate (29.5 g, 184.1 mmol) in 75 mL anhydrous.DMF was heated at 130° C. overnight under a nitrogen atmosphere. The reaction mixture was cooled to rt, and then 1 N HCl solution (200 mL) was added with stirring to induce precipitation. After the mixture was stirred for 30 minutes, the solid precipitate was collected by filtration and rinsed with water. The filter cake was dissolved in 100 mL EtOAc, and the solution was dried over Na2SO4. EtOAc was removed by rotary evaporation, and the residue was dried in vacuo to afford the desired product as a white solid (18.0 g, 99percent). 1H NMR (DMSO-d6) delta 14.00 (bs, 1H), 8.20 (s, 1H), 7.70 (d, 1H), 7.40 (d, 1H); GC-EIMS m/z 235 (M+).
  • 23
  • [ 39885-50-2 ]
  • [ 87-13-8 ]
  • [ 259683-65-3 ]
YieldReaction ConditionsOperation in experiment
at 190℃; for 2h; EXAMPLE 59 8-Chloro-N-((4-chlorophenyl)methyl)-4-hydroxy-5-trifluoromethyl-3-quinolinecarboxamide [] A mixture of 2-chloro-5-trifluoromethylaniline (3.91 g) and diethyl ethoxymethylenemalonate (4.0 mL) is heated at 190°C for 2 h and is then diluted with diphenyl ether (30 mL). The mixture is allowed to cool to rt, filtered, and the white solid is washed with hexane (2 x 10 mL) to afford 1.632 g of the diethyl aminomethylenemalonate. The resulting intermediate (2.63 g) is suspended in diphenyl ether (30 mL) and heated to reflux with a Dean-Stark trap for 3 h. The mixture is allowed to cool to rt and is then poured into hexane (50 mL). The solid is filtered and then washed with hexane (20 mL) and hexane/diethyl ether (1/1, 20 mL) to afford 1.273 g of the quinolinecarboxylate ethyl ester. The ester (400 mg) and 4-chlorobenzylamine (1.52 mL) are heated at 190 °C for 1 h. The resulting mixture is diluted with toluene (4 mL), allowed to cool to rt, and then poured into hexane (50 mL). The solvent is decanted and the remaining oil is crystallized (acetic acid, water) to afford 285 mg of the title compound as a brown solid. Physical characteristics are as follows: Mp 270-1 °C.1H NMR (300 MHz, DMSO) delta 12.33, 10.06, 8.68, 8.10, 7.86, 7.36, 4.52.13C NMR (100 MHz, DMSO) delta 175.05, 164.07, 144.36, 139.12, 138.20, 132.42, 131.85, 129.84, 128.77, 128.44, 126.70 (q), 125.84, 125.20, 122.22, 113.75, 42.00.IR (mull) 3187, 3091, 2925, 2855, 1657, 1604, 1567, 1531, 1462, 1417, 1377, 1366, 1348, 1307, 1272, 1210, 1158, 1139, 1128, 1106, 854, 841, 802, 726 cm-1.Anal. Found: C, 52.12; H, 2.78; N, 6.70; Cl, 16.85.MS (ESI-) for C18H11Cl2F3N2O2m/z 412 (M-H)-.
  • 24
  • [ 871819-61-3 ]
  • [ 39885-50-2 ]
  • N-[2-chloro-4-(trifluoromethyl)phenyl]-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
A mixture of 4-chloro- I-methyl-7-(4-morpholinylcarbonyl)- lH-pyrrolo[3,2-c]py/dine (100 mg), 2-chloro-4-trifluoromethylaniline (80 mg), cesium carbonate (168 mg), tris (dibenzylideneacetone)dipalladium (0) (3.4 mg) and 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (2.3mg) in 1,4-dioxan ( 2 ml) was heated to 100°C under nitrogen for 2h. Added tris(dibenzylideneacetone)dipalladium (0) (10 mg) and 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (7mg) and continued heating at 100°C under nitrogen over night. The reaction mixture was diluted with dichloromethane and washed with water then dried (MgS04), filtered and evaporated. Purification and salt formation was as described in Example 101 to afford the title compound as a white solid (64 mg). LC/MS t = 2.14 min, [MH+] 439 consistent with molecular formula C20H1835ClF3N4O2.
  • 25
  • [ 689299-84-1 ]
  • [ 39885-50-2 ]
  • N-[3-chloro-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenylamino)-acetamide [ No CAS ]
  • 26
  • [ 39885-50-2 ]
  • [ 86398-98-3 ]
YieldReaction ConditionsOperation in experiment
2-Chloro-4-trifluoromethylphenylhydrazine, m.p. 38°-39° C., in the form of a colorless solid, from 2-chloro-4-trifluoromethylaniline.
  • 27
  • [ 39885-50-2 ]
  • [ 634-93-5 ]
  • [ 120068-81-7 ]
YieldReaction ConditionsOperation in experiment
5-Amino-1-(2-chloro-4-trifluoromethylphenyl)-3-cyanopyrazole in the form of an orange crystalline solid, m.p. 133°-135° C., from 2-chloro-4-trifluoromethylaniline. 5-Amino-3-cyano-1-(2,4,6-trichlorophenyl)pyrazole in the form of a light brown solid, m.p. 155-156° C., from 2,4,6-trichloroaniline.
5-Amino-1-(2-chloro-4-trifluoromethylphenyl)-3-cyanopyrazole in the form of an orange crystalline solid, m.p. 133-135°C, from 2-chloro-4-trifluoromethylaniline. 5-Amino-3-cyano-1-(2,4,6-trichlorophenyl)pyrazole in the form of a light brown solid, m.p. 155-156°C, from 2,4,6-trichloroaniline
  • 28
  • [ 31825-28-2 ]
  • [ 39885-50-2 ]
YieldReaction ConditionsOperation in experiment
With HF; 2) 2-Chloro-4-trifluoromethylaniline 135 g (0.5 mol) of 2-chloro-4-trichloromethylphenyl isocyanate and 500 g of anhydrous HF are reacted at 70° C. for 4 hours in a pressure vessel in the same manner as in Example 1 and subsequently worked up in a completely analogous manner. The product (76 g, 78percent of theory) is once again obtained by fractional distillation. Its identity and purity were demonstrated by GC/NMR (1 H NMR (CDCl3): delta=7.5, 1 H, br s; delta=7.2, 1 H, br s; delta=6.6, 1 H, d, 8.6 Hz; delta=4.35, 2 H, br s).
  • 29
  • [ 777-44-6 ]
  • [ 39885-50-2 ]
  • [ 95-50-1 ]
  • N-(2-chloro-4-trifluoromethylphenyl)-3-trifluromethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.2 g (55%) With pyridine; SYNTHESIS EXAMPLE 1 Synthesis of N-(2-chloro-4-trifluoromethylphenyl)-3-trifluromethylbenzenesulfonamide (Compound 1) In a 400 ml flask, 200 ml of o-dichlorobenzene, 1 ml of pyridine and 2.0 g (0.01 mole) of 2-chloro-4-trifluoromethylaniline were charged. While stirring the contents at room temperature, 2.5 g (0.01 mole) of 3-trifluoromethylbenzenesulfonyl chloride was added gradually over 5 minutes. Thereafter, the reaction mixture was heated and stirred for 6 hours under reflux (175-180° C.) to complete the reaction. After cooling the reaction mixture to room temperature, it was thoroughly washed first with dilute hydrochloric acid and then with water. Subsequent to its dehydration with sodium sulfate, o-dichlorobenzene was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (eluent: benzene) to isolate the intended Compound 1. m.p. 121°-123° C., yield 2.2 g (55percent).
  • 30
  • [ 54090-08-3 ]
  • [ 39885-50-2 ]
  • [ 95-50-1 ]
  • N-(2-chloro-4-trifluoromethylphenyl)-2-chloro-5-trifluoromethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.2 g (50%) With pyridine; SYNTHESIS EXAMPLE 2 Synthesis of N-(2-chloro-4-trifluoromethylphenyl)-2-chloro-5-trifluoromethylbenzenesulfonamide (Compound 2) In a 400 ml flask, 200 ml of o-dichlorobenzene, 1 ml of pyridine and 2.0 g (0.01 mole) of 2-chloro-4-trifluoromethylaniline were charged. While stirring the contents, 2.8 g (0.01 mole) of 2-chloro-5-trifluoromethylbenzenesulfonylchloride was added dropwise at room temperature over 5 minutes. Thereafter, the reaction mixture was heated and stirred for 8 hours under reflux (175°-180° C.). After cooling the reaction mixture to room temperature, it was thoroughly washed first with dilute hydrochloric acid and then with water. Subsequent to its dehydration with anhydrous sodium sulfate, o-dichlorobenzene was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (eluent: benzene) to isolate the intended Compound 2. m.p. 122°-123° C., yield 2.2 g (50percent).
  • 31
  • [ 89-55-4 ]
  • [ 39885-50-2 ]
  • 5-bromo-N-[2-chloro-4-(trifluoromethyl)phenyl]-2-hydroxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34.9% Example 129 5-Bromo-N-[2-chloro-4-(trifluoromethyl)phenyl]-2-hydroxybenzamide (Comopund No. 129). Using 5-bromosalicylic acid and <strong>[39885-50-2]2-chloro-4-(trifluoromethyl)aniline</strong> as the raw materials, the same operation as the example 16 gave the title compound. Yield: 34.9percent. 1H-NMR(DMSO-d6): delta 7.04(1H, d, J=8.7Hz), 7.64(1H, dd, J=8.7, 2.7Hz), 7.79(1H, dd, J=9.0, 2.1Hz), 7.99(1H, d, J=2.1Hz), 8.11(1H, d, J=2.4Hz), 8.73(1H, d, J=9.0Hz), 11.15(1H, s), 12.42(1H, s).
  • 32
  • ethyl (2E)-3-(4-(2-methoxyethoxy)-2-[(trifluoromethyl)sulfonyl]oxy}phenyl)acrylate [ No CAS ]
  • [ 39885-50-2 ]
  • [ 926297-11-2 ]
YieldReaction ConditionsOperation in experiment
54% With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;palladium diacetate; In tetrahydrofuran; for 8h;Heating / reflux; To a solution of ethyl (2E) -3- (4- (2-methoxyethoxy) -2- { [ (trifluoromethyl) sulfonyl] oxy}phenyl) acrylate (1.66 g) in tetrahydrofuran (20 ml) were added 2-chloro-4- . (trifluoromethyl) aniline (1.89 g) , racemic-2, 2' - bis(diphenylphosphino)-l,l'-binaphthyl (519 mg) , palladium acetate (140 mg) and cesium carbonate (2.06 g) , and the mixture was heated under reflux for 8 hr. After cooling, water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl -acetate layer was washed with saturated brine, dried (MgSO4) , and concentrated. The obtained residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:3, v/v) to give ethyl (2E) -3- [2-{ [2-chloro-4- (trifluoromethyl) phenyl] amino} -4- (2- methoxyethoxy) phenyl] acrylate (1.00 g, yield: 54percent) as yellow crystals.1H-NMR (300 MHz, CDCl3) 6:1-29 (3 H, t, J = 7.2 Hz), 3.44 (3 H, s) , 3.73 - 3.79 (2 H, m) , 4.16 - 4.27 (4 H, m) , 6.23 (1 H, s) , 6.34 (1 H, d, J = 15.9 z) , 6.55 - 6.59 (1 H, m) , 6.85 - 6.91 (2 H, m),.7.32 - 7.62 (-3 H, m) , 7.77 (I H, d, J = 15.9 Hz)..
  • 33
  • [ 1059176-81-6 ]
  • [ 39885-50-2 ]
  • [ 1059176-82-7 ]
  • 34
  • [ 421-83-0 ]
  • [ 39885-50-2 ]
  • (2-Cl-4-CF3C6H3NH3)Cl [ No CAS ]
  • [ 27573-83-7 ]
  • 35
  • [ 335-05-7 ]
  • [ 39885-50-2 ]
  • (2-Cl-4-CF3C6H3NH3)F [ No CAS ]
  • [ 27573-83-7 ]
  • 36
  • [ 913299-00-0 ]
  • [ 39885-50-2 ]
  • [ 1022248-87-8 ]
YieldReaction ConditionsOperation in experiment
32% A mixture of 2-chloro-7- ( 1-ethylpropyl) -4-methoxy-l- methyl-ltf-benzimidazole (200 mg, 0.750 mmol) and 2-chloro- 4-trifluoromethylaniline (450 mg, 2.25 mmol) in l-methyl-2- pyrrolidone (0.5 mL) was stirred at 12O0C for 96 h under nitrogen atmosphere. The mixture was diluted with aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a 5-30percent ethyl acetate/n- hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from methanol to afford the title compound as colorless crystals(103 mg, 32percent) . mp 170-1710C.1H NMR (CDCl3) delta 0.85 t, J = 7.5 Hz, 6H), 1.60-1.85 (m, 4H), 3.15-3.20 (m, IH) 3.88 (s, 3H), 4.00 (s, 3H), 6.71 (d, J = 8.4 Hz, IH) , 6.85 (s, IH), 6.99 (d, J = 7.8 Hz, IH), 7.50 (d, J = 8.4 Hz, IH) , 7.65 (s, IH), 8.00 (d, J = 7.8 Hz, IH) .MS Calcd. : 425; MS Found: 426 (M+H) , 428.
  • 37
  • [ 1051372-42-9 ]
  • [ 39885-50-2 ]
  • [ 1051372-36-1 ]
  • 38
  • [ 1189816-68-9 ]
  • [ 39885-50-2 ]
  • [ 1189812-82-5 ]
YieldReaction ConditionsOperation in experiment
36% Example 199; 3-(9-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chloro-4-(trifluoromethyl)phenyl)-4H-1,2,4-triazole 289; A microwave tube charged with 2-(9-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulen-2-yl)-[1,3,4]oxadiazole (200 mg; 0.57 mmol), 2-chloro-4-trifluoromethylaniline (0.12 ml; 0.86 mmol), TFA (64 mul; 0.86 mmol) and toluene (1.5 ml) was heated in a microwave at 160° C. for 30 min. The reaction mixture was basified with DIPEA (0.2 ml), volatiles removed in vacuo and the residue purified by prep. LCMS to give 289 as a white solid (109 mg; 36percent). deltaH (400 MHz, CDCl3) 3.13 (t, J=5.2, 2H), 4.29 (t, J=5.2, 2H), 6.89-6.93 (m, 2H), 7.24-7.28 (m, 1H), 7.62-7.67 (m, 2H), 7.80-7.83 (m, 1H), 7.98 (s, 1H), 8.26 (s, 1H). [M+H]+: 527
  • 39
  • [ 39885-50-2 ]
  • [ 1065102-88-6 ]
YieldReaction ConditionsOperation in experiment
97% EXAMPLE 4Preparation of 2-chloro-6-iodo-4-(trifluoromethyl)benzenamineIodine monochloride (17.2 g, 108 mmol) in hydrochloric acid (36percent, 21.4 g) and water (35 mL) was added dropwise to <strong>[39885-50-2]2-chloro-4-(trifluoromethyl)benzenamine</strong> (20.0 g, 102 mmol) in hydrochloric acid (36percent, 20.7 g) and water (140 mL). The mixture was warmed to 50 0C for a total of 8 h. Sodium hydroxide (50percent, 33.5 g, 419 mmol) was added to the mixture at room temperature. The mixture was extracted with dichloromethane (2 x 250 mL), and the extracts were dried and evaporated to give the product as an oil (31.83 g, 97percent yield). 1H NMR (CDCl3) 7.78 (s, IH), 7.5 (s, IH), 4.87 (br s, 2H).
  • 40
  • [ 39885-50-2 ]
  • [ 106-95-6 ]
  • [ 1004547-95-8 ]
  • 41
  • [ 2314-97-8 ]
  • [ 95-51-2 ]
  • [ 433-94-3 ]
  • [ 39885-50-2 ]
  • 42
  • [ 263155-95-9 ]
  • [ 39885-50-2 ]
  • [ 1226644-48-9 ]
  • 43
  • [ 112729-27-8 ]
  • [ 39885-50-2 ]
  • [ 1242652-46-5 ]
  • 44
  • [ 39885-50-2 ]
  • [ 76-05-1 ]
  • [ 185315-34-8 ]
  • 45
  • [ 328-84-7 ]
  • [ 39885-50-2 ]
YieldReaction ConditionsOperation in experiment
84% With potassium fluoride; ammonia; In dimethylsulfone; at 30 - 235℃; for 6h;Autoclave;Product distribution / selectivity; Example -43,4-Dichlorobenzotrifluoride (75.4 g) was added to 210 g of dimethylsulfone 30.45 g of calcined potassium fluoride in an autoclave. The ammonia gas (1 to 1.2 m/m) was passed at 30°C. The reaction mixture was maintained at 235°C and 25-26 kg/cm2 for 6 hrs. After work up and fractionation the yield of 2-chloiO-4-trifluoromethylaniline was 84percent based on 3,4- dichlorobenzotrifluoride consumed
84% With potassium fluoride; ammonia; In dimethyl sulfoxide; at 30 - 235℃; under 18389.3 - 19124.9 Torr; for 6h;Autoclave;Product distribution / selectivity; Example -4; 3,4-Dichlorobenzotrifluoride (75.4 g) was added to 210 g of dimethylsulfone 30.45 g of calcined potassium fluoride in an autoclave. The ammonia gas (1 to 1.2 m/m) was passed at 30°C. The reaction mixture was maintained at 235°C and pressure of 25-26 kg/cm for 6 hrs. After work up and fractionation the yield of 2-chloro-4-trifluoromethylaniline was 84percent based on 3,4-dichlorobenzotrifluoride consumed.
84% With potassium fluoride; dimethylsulfone; ammonia; at 30 - 235℃; under 18751.9 - 19502 Torr; for 6h;Autoclave; Example 4 3,4-Dichlorobenzotrifluoride (75.4 g) was added to 210 g of dimethylsulfone delta 30.45 g of calcined potassium fluoride in an autoclave. The ammonia gas (1 to 1.2 m/m) was passed at 30° C. The reaction mixture was maintained at 235° C. and pressure of 25-26 kg/cm for 6 hrs. After work up and fractionation the yield of 2-chloro-4-trifluoromethylaniline was 84percent based on 3,4-dichlorobenzotrifluoride consumed.
  • 46
  • [ 39885-50-2 ]
  • [ 24279-39-8 ]
YieldReaction ConditionsOperation in experiment
95% Example- 6<strong>[39885-50-2]2-Chloro-4-trifluoromethylaniline</strong> (0.88m), 2-chloro-5-trifluoromethyl aniline (0.1 1 7 m) and 102 g of N-methyl pyrrolidone (NMP) was mixed with 500 ml chlorobenzene. Sulfuryl chloride (148.4 g) was added to the mixture at 55-60°C over a period of 4 hours and the reaction mixture was maintained at 55-60°C for 2 hours. Reaction medium on treatment with water and 5N NaOH followed by fractionation gave 0.84 m of 2,6-dichloro-4- trifluoromethylaniline, 95percent yield on 2-chloro-4 rifluoromethylaniline.
95% With 1-methyl-pyrrolidin-2-one; sulfuryl dichloride; In 1-methyl-pyrrolidin-2-one; chlorobenzene; at 55 - 60℃; for 8h; Example 6 A mixture (301 g) of 2-chloro-4-trifluoromethylaniline, 2-chloro-5-trifluoromethylaniline and N-methylpyrrolidone (NMP) (1.06 m/m) was mixed with 500 ml chlorobenzene. Sulfuryl chloride (148.4 g) was added to the mixture at 55-60° C. over a period of 4 hours and the reaction mixture was maintained at 55-60° C. for 4 hours. Reaction medium on treatment and fractionation gave 0.84 m of 2,6-dichloro-4-trifluoromethylaniline, 95percent yield on <strong>[39885-50-2]2-chloro-4-trifluoromethyl aniline</strong>.
  • 47
  • [ 328-84-7 ]
  • [ 39885-50-2 ]
  • [ 121-50-6 ]
YieldReaction ConditionsOperation in experiment
77%; 13% With potassium fluoride; ammonia; In 1-methyl-pyrrolidin-2-one; at 245 - 250℃; under 22067.2 - 29422.9 Torr; for 10h;Autoclave; Example- 1; N-methylpyrrolidone (1050 ml) was charged in an autoclave along with 102 g anhydrous activated potassium fluoride, 377 g 3,4- dichlorobenzotrifluoride was added. Ammonia (158 g) gas was passed in the reactor from the pressure pot at ambient temperature. The content of the reactor was heated to 245-250°C over a period of 2 hours to get reactor pressure of 30-32 kg/cm2. Excess NH3 was fed from the pressure pot to maintain the reactor pressure at 38-40 kg/cm at 245-250°C liquid temperature. Reaction mixture was maintained at 245-250°C and at 38-40 kg/cm2 pressure for further 8 hours. Reaction mixture was cooled to ambient temperature and NH3 was vented and recovered. Reaction mixture was filtered and on fractionation gave 77percent yield of 2-chloro-4- trifluoromethylaniline and 13percent yield of 2-chloro-5-trifluoro methyl aniline based on consumed 3,4-dichlorobenzotrifluoride.
77%; 13% With 1-methyl-pyrrolidin-2-one; potassium fluoride; ammonia; at 245 - 250℃; under 22502.3 - 30003 Torr; for 10h;Autoclave; Example-1 N-methylpyrrolidone (1050 ml) was charged in an autoclave along with 102 g anhydrous activated potassium fluoride, 377 g 3,4-dichlorobenzotrifluoride was added. Ammonia (158 g) gas was passed in the reactor from the pressure pot at ambient temperature. The content of the reactor was heated to 245° C.-250° C. over a period of 2 hours to get reactor pressure of 30-32 kg/cm2. Excess NH3 was fed from the pressure pot to maintain the reactor pressure at 38-40 kg/cm2 at 245-250° C. liquid temperature. Reaction mixture was maintained at 245-250° C. and at 38-40 kg/cm2 pressure for further 8 hours. Reaction mixture was cooled to ambient temperature and NH3 was vented and recovered. Reaction mixture was filtered and on fractionation gave 77percent yield of 2-chloro-4-trifluoromethylaniline and 13percent yield of 2-chloro-5-trifluoromethyl aniline based on consumed 3,4-dichlorobenzotrifluoride.
  • 48
  • [ 39885-50-2 ]
  • [ 72773-04-7 ]
  • [ 90720-05-1 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 70℃; for 23h; Intermediate 1 : [2-Chloro- -(trifluoromethyl)phenyl]formamide; To a solution of <strong>[39885-50-2]2-chloro-4-(trifluoromethyl)aniline</strong> (500 mg, 2.56 mmol) in tetrahydrofuran (THF) (8 imL) was added 1 H-1 ,2,3-benzotriazole-1 -carbaldehyde (489 mg, 3.32 mmol, Sigma-Aldrich). The reaction mixture was heated to 70C and stirred for 18 hours. To the reaction mixture was added 1 H-1 ,2,3-benzotriazole-1 - carbaldehyde (1.16mmol, 245mg) and the reaction mixture heated to 70C for a further 5 hours. The reaction mixture was concentrated under vacuum and the residue partitioned between DC (20mL) and 2N HCI (10mL). The organic layer was collected via a hydrophobic frit and the solvent removed under vacuum. The crude product was purified by silica chromatography (Biotage SP4, eluting iso- hexane (5 column volumes) followed by a gradient from 0-20% EtOAc in iso-hexane (over 15 column volumes)) to yield the title compound as a solid (0.445g)1 H NMR (400 MHz, Chloroform-D) delta ppm 7.55 (m, 1 H) 7.68 (d, J=1 .5 Hz, 1 H) 7.83 (br.s, 1 H) 8.56 (d, J=1 .3 Hz, 1 H) 8.62 (d, J=8.Q Hz, 1 H)MS ES-ve m/z 222, 224 (M+H)
  • 49
  • [ 39885-50-2 ]
  • [ 1354945-98-4 ]
  • 50
  • [ 39885-50-2 ]
  • C8H3ClF3N [ No CAS ]
  • 51
  • [ 50329-91-4 ]
  • [ 39885-50-2 ]
  • [ 1394232-24-6 ]
  • 53
  • [ 39885-50-2 ]
  • [ 634185-63-0 ]
  • 54
  • [ 321-14-2 ]
  • [ 39885-50-2 ]
  • [ 934192-70-8 ]
YieldReaction ConditionsOperation in experiment
43% With pyridine; phosphorus trichloride; In toluene; for 12h;Inert atmosphere; Reflux; General procedure: The salicylic acid (1.2 equiv) was added to a mixture of toluene (0.3 M), aniline (1.0 equiv), phosphorus trichloride (1.1 equiv), and pyridine (0.05 equiv) in a Radley?s Carousel reaction tube (modified from Itai et al.20). The mixture was refluxed under nitrogen for 12 h then cooled to room temperature. Aqueous sodium bicarbonate was added dropwise to attain pH 6?7. The resultant mixture was extracted with EtOAc. The organic extracts were combined, dried (MgSO4), and concentrated under vacuum. After chromatography (1:10 EtOAc:Hex) compounds were recrystallized (EtOAc/Hex).
With phosphorus trichloride; In 5,5-dimethyl-1,3-cyclohexadiene; for 1h;Inert atmosphere; Reflux; General procedure: Anilide synthesis. General method. To a 100 mL flask equipped with a reflux condenser was added 5-chloro-2-hydroxybenzoic acid (1 equiv), the aniline derivative (1 equiv), and dry xylenes(stored over 3A molecular sieves, 40 mL per gram of 5-chloro-2-hydroxybenzoic acid) under an Argon atmosphere. The mixture was heated to reflux, and PCl3 (0.4 equiv) was added rapidly via syringe. The mixture was heated at reflux for 1 h and cooled to room temperature. Water (40 mL per gram of 5-chloro-2-hydroxybenzoic acid) was added and the resultant heterogeneous mixture stirred rapidly for 1 h. Saturated sodium bicarbonate was added to a final pH of 3?4, and the mixture stirred rapidly overnight. The solids were filtered and washed sequentially with water, toluene and hexane. Samples were analyzed by NMR, HPLC/mass spectrometry and TLC. Purification by crystallization or column chromatography on silica gel was performed when purity was less than 95percent by LC. Additional experimental procedures and analytical data are provided in Supplemental data.
With phosphorus trichloride; In 5,5-dimethyl-1,3-cyclohexadiene; for 1h;Molecular sieve; Inert atmosphere; Reflux; General procedure: Example 4. Anilide Synthesis (0233) (0234) General Method: (0235) To a 100 mL flask equipped with a reflux condenser was added 5-chloro-2-hydroxybenzoic acid (1 equiv.), the aniline derivative (1 equiv.), and dry xylenes (stored over 3 A molecular sieves, 40 mL per gram of 5-chloro-2-hydroxybenzoic acid) under an atmosphere of argon. The mixture was heated to reflux, and PCl3 (0.4 equiv.) was added rapidly via syringe. The mixture was heated at reflux for 1 hour and cooled to room temperature. Water (40 mL per gram of 5-chloro-2-hydroxybenzoic acid) was added and the resultant heterogeneous mixture stirred rapidly for 1 hour. Saturated sodium bicarbonate was added to a final pH of 3-4, and the mixture stirred rapidly overnight. The solids were filtered and washed sequentially with water, toluene and hexane. Samples were analyzed by NMR, HPLC/mass spectrometry and TLC. Purification by crystallization or column chromatography on silica gel was performed when purity was less than 95percent by LC. HPLC/MS was accomplished using an Agilent spectrometer ?6310 Ion trap. Mass ions (m/z) detected in positive ionization mode are M+; in negative ionization mode, mass ions (m/z) are M?.
With phosphorus trichloride; In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; for 5h;Reflux; Both compounds were synthesized using a one-step reaction. For the synthesis of Compound 7, commercially- available 5-chlorosalicylic acid was coupled with <strong>[39885-50-2]2-chloro-4-trifluoromethyl aniline</strong> using a 2 M solution of phosphorus trichloride in dichloromethane. Xylene was used as the solvent for the reaction and the reaction mixture was refluxed for 5 hours (or until the reactants disappeared). The hot solution was transferred and brought to room temperature for the product to precipitate out of the solution. The precipitate was then re-dissolved in ethyl acetate and recrystallized to obtain the pure Compound 7.

  • 55
  • [ 39885-50-2 ]
  • [ 5714-17-0 ]
  • [ 1422955-25-6 ]
  • 56
  • [ 39885-50-2 ]
  • [ 120067-83-6 ]
  • 57
  • [ 39885-50-2 ]
  • [ 1423126-81-1 ]
  • 58
  • [ 39885-50-2 ]
  • [ 1423126-74-2 ]
  • 59
  • [ 32315-10-9 ]
  • [ 39885-50-2 ]
  • [ 51488-22-3 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 0℃; for 1h; General procedure: Aniline (140mg, 1.5mmol) and Et3N (202mg, 2mmol) were dissolved in 5mL of dichloromethane and slowly added dropwise to a solution of triphosgene (BTC) (223mg, 0.75mmol) in 10mL of dichloromethane at 0°C. The mixture was then stirred at 0°C for 1h. Then, 5a (300mg, 1mmol) in 1mL of DMF was added at 0°C, and the mixture was then stirred at room temperature for 30min, and the solvent was distilled with a rotary evaporator. The residue was washed with water (10mL×3) and purified via silica gel flash column chromatography to afford 1-(3-((2S,5S)-5-((1H-indol-3-yl)methyl)-3,6-dioxopiperazin-2-yl)propyl)-3-phenylurea (6a) as a pale powder in 74percent yield. Compounds 6b?v, 7a?k and 8a?k were prepared similar to 6a.
  • 60
  • [ 39885-50-2 ]
  • [ 1312175-25-9 ]
  • 61
  • [ 39885-50-2 ]
  • 2-halopyridine [ No CAS ]
  • [ 1439922-52-7 ]
YieldReaction ConditionsOperation in experiment
89% With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 14h;Inert atmosphere; General procedure: A mixture of aniline (3mmol), 2-halopyridine (3mmol), Cs2CO3 (9mmol), Pd(OAc)2 (0.12mmol), and BINAP (0.12mmol) in toluene (5mL) under an argon atmosphere was stirred at 100°C for 14h. After cooling, the reaction mixture was diluted with ethyl acetate and filtered. The filtrate was evaporated and the residue purified by column chromatography on silica gel eluting with petroleum ether (bp 60?80°C)/ethyl acetate to give the desired products.
  • 62
  • [ 1423162-03-1 ]
  • [ 39885-50-2 ]
  • [ 1450923-29-1 ]
YieldReaction ConditionsOperation in experiment
0.332 g With lithium hexamethyldisilazane; In tetrahydrofuran; at 0℃; for 0.5h; A 50-mL round-bottom flask was charged with INTERMEDIATE S (0.645 g, 1.419 mmol), 4-amino-3-chlorobenzotrifluoride (0.235 mL, 1.703 mmol), and THF (7.10 mL) to give a yellow solution. The flask was cooled in an ice-bath for 5 min, then lithium bis(trimethylsilyl)amide (1M in THF) (4.26 mL, 4.26 mmol) was added dropwise over 1 minute to give a dark maroon mixture. The reaction was stirred for 30 minutes at 0 °C. The mixture was diluted with saturated aq. ammonium chloride solution, then with water, and extracted with EtOAc (3x). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on a 40g silica gel column with 0 to 50percent EtO Ac/Heptane gradient elution to give 4-((2-chloro-4-(trifluoromethyl)phenyl)amino)-N-(2,4-dimethoxybenzyl)-3-nitro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.332 g, 0.527 mmol) (INTERMEDIATE T) as a bright-yellow solid, m/z (ESI) 652.1 (M+Na)+
  • 63
  • [ 39885-50-2 ]
  • [ 1245737-88-5 ]
  • 64
  • [ 39885-50-2 ]
  • [ 1885-14-9 ]
  • [ 259655-30-6 ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 0 - 20℃; General procedure: The appropriate aromatic amine (1mmol) was dissolved under Ar in dry 47 CH2Cl2 (3mL), cooled in an ice bath and treated with a solution of 12 phenyl chloroformiate (190muL, 1.5mmol) and 48 pyridine (200muL, 2.5mmol) in dry CH2Cl2 (1mL). The mixture was then stirred for 2hat room temperature and then worked up. The residue was subjected to column chromatography on silica gel (elution with hexane-EtOAc 9:1) to afford the corresponding 13 urethane.
  • 65
  • [ 140-89-6 ]
  • [ 39885-50-2 ]
  • [ 401567-22-4 ]
  • 66
  • [ 39885-50-2 ]
  • C36H44F3N6O3S3(1+)*Cl(1-) [ No CAS ]
  • 67
  • [ 39885-50-2 ]
  • C26H30F3N4OS2(1+)*Cl(1-) [ No CAS ]
  • 68
  • [ 39885-50-2 ]
  • C31H38F3N4O3S2(1+)*Br(1-) [ No CAS ]
  • 69
  • [ 39885-50-2 ]
  • C26H30F3N4OS2(1+)*C2F3O2(1-) [ No CAS ]
  • 70
  • [ 39885-50-2 ]
  • [ 401567-23-5 ]
  • 71
  • [ 39885-50-2 ]
  • C10H9F3NS2(1+)*C7H7O3S(1-) [ No CAS ]
  • 72
  • [ 39885-50-2 ]
  • C14H11F3N2OS3 [ No CAS ]
  • 73
  • [ 39885-50-2 ]
  • C15H14F3N2OS3(1+)*C7H7O3S(1-) [ No CAS ]
  • 74
  • [ 1897-45-6 ]
  • [ 39885-50-2 ]
  • [ 1416419-65-2 ]
YieldReaction ConditionsOperation in experiment
75% General procedure: Substituted aniline (5mumol) was dissolved in 5mL of DMF, and sodium hydroxide (10mumol) was added to the solution. The solution was stirred for 10min, and corresponding intermediate phthalonitrile (or isophthalonitrile or terephthalonitrile) (5mumol) was then added. The reaction mixture was stirred at 60°C and monitored by TLC. After completion of the reaction (2h), the mixture was then added to 50mL water and extracted with ethyl acetate (3mL×100mL). The combined extracts were washed with brine, dried (anhydrous magnesium sulfate), and filtered. The filtrate was then evaporated and the crude product was purified via silica gel column chromatography, using a 1:4 (v/v) mixture of ethyl acetate and petroleum ether (boiling point range: 60?90°C) of the eluting solution to obtain the title compound 3; except for 3h, 3i and 3k.
  • 75
  • [ 39885-50-2 ]
  • tetrafluoroisophthalonitrile [ No CAS ]
  • [ 1416420-30-8 ]
  • 76
  • [ 3900-89-8 ]
  • [ 39885-50-2 ]
  • 2′-chloro-5′-(trifluoromethyl)-[1,1′-biphenyl]-2-amine [ No CAS ]
  • 77
  • [ 3900-89-8 ]
  • [ 39885-50-2 ]
  • [ 2467-83-6 ]
  • 78
  • [ 39885-50-2 ]
  • [ 1355001-50-1 ]
  • 79
  • [ 39885-50-2 ]
  • C16H11F6NO [ No CAS ]
  • 80
  • [ 39885-50-2 ]
  • C16H9F6NO [ No CAS ]
  • 81
  • [ 39885-50-2 ]
  • C22H14F6N2O2 [ No CAS ]
  • 82
  • [ 39885-50-2 ]
  • C22H16F6N2 [ No CAS ]
  • 84
  • [ 39885-50-2 ]
  • C22H14F6IN [ No CAS ]
  • 85
  • [ 39885-50-2 ]
  • C27H24BF6NO2 [ No CAS ]
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