Structure of 393-49-7
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CAS No. : | 393-49-7 |
Formula : | C7H5F3N2O2 |
M.W : | 206.12 |
SMILES Code : | NC1=C(C=CC(=C1)[N+]([O-])=O)C(F)(F)F |
MDL No. : | MFCD00007365 |
InChI Key : | LGHXDTHJGNCRKT-UHFFFAOYSA-N |
Pubchem ID : | 2737719 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40.5% | With caesium carbonate;palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; at 80℃; for 0.416667h;microwave irradiation; | Example 13: Synthesis of Compound XIII- 11; Step 1: Synthesis of 2-((5-chloro-2-((5-nitro-2-(trifluoromethyI)phenyl)aminopyrimidin-4- yl)amino)-N-methylbenzamide (3); 5-Nitro-2-(trifluoromethyl)aniline (2, 0.1 g, 0.4851 mmol), 2-((2,5-dichloropyrimidin-4- yl)amino)-N-methylbenzamide (1, 0.144 g, 0.4851 mmol), palladium acetate (0.054 g, 0.2425 mmol), Xantphos (0.084 g, 0.1455 mmol) and cesium carbonate (0.474 g, 1.455 mmol) were taken in dry THF (5 mL). Reaction mixture was irradiated under microwave condition at 80 C for 25 min. Reaction was monitored by TLC and LCMS. After completion of the reaction, brine solution was added, extracted with ethyl acetate. Organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crude product was purified by column chromatography using 2% MeOH:DCM to afford 2-((5- chloro-2-((5-nitro-2-(trifluoromethyl)phenyl) amino) pyrimidin-4-yl)amino)-N-methylbenzamide (3, 0.1 1 1 g, 40.5%). NMR (400 MHz, CDCI3): δ 1 1.20 (s, 1 H), 9.20 (s, 1 H), 8.40-8.35 (d, 1 H), 8.20 (s, I H), 7.90-7.85 (d, I H), 7.80-7.00 (d, I H), 7.50-7.45 (d, I H), 7.40-7.35 (s, I H), 7.34-7.30 (t, I H), 7.10- 7.00 (t, I H), 6.20 (bs, I H), 3.00 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 12.0h; | N-(5-nitro-2-(trifluoromethyl)phenyl)acrylamide (2): To a solution of 5-nitro-2- (trifluoromethyl)aniline (900 mg, 4.30 mmol) in dichloromethane (20 mL), diisopropylethylamine (1.7 g, 13.0 mmol) and acryloyl chloride (2.0 g, 22.0 mmol) were added at 0 C. The resulting reaction mixture was stirred at room temperature for 12 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue showed mixture of mono and diacylated compounds. The residue was treated with potassium carbonate (200 mg, 1.4 mmol) in methanol (5 mL) for 2 h at room temperature. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to afford 2 (350 mg, 31%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 5.83-5.86 (dd, J = 2.0, 10.2 Hz, 1H), 6.28-6.33 (dd, J = 2.0, 17.0 Hz, 1H), 6.56-6.63 (dd, J = 10.2, 17.0 Hz, 1H), 8.05- 8.07 (d, J = 9.0 Hz, 1H), 8.22-8.24 (dd, J = 1.5, 9.0 Hz, 1H), 8.44-8.45 (d, J = 2.0 Hz, 1H), 10.07 (s, 1H). MS m/z (M-H): 259.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With ammonia; In methanol; at -78 - 100℃; for 16.0h; | 5-nitro-2-(trifluoromethyl)aniline (1): Solution of 2-fluoro-4-nitro-l- (trifluoromethyl)benzene (1.4 g, 6.7 mmol) in methanol (10 mL) was purged with ammonia at - 78 C for 10 min followed by heating at 100 C for 16 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was diluted with water and extracted with ethyl acetate. The organic layer was washed once with brine and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford 1 (900 mg, 65%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 6.31 (s, 2H), 7.31-7.34 (dd, J = 1.4, 9.0 Hz, 1H), 7.58-7.60 (d, J = 9.0 Hz, 1H), 7.67 (d, J = 2.2 Hz, 1H). MS m/z (M-H): 205.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In iso-butanol;Reflux; | General procedure: 0.5 g (0.0039 mol) of barbituric acid or thiobarbituric acid was added in 2-butanol (8-10 ml) and warmed till the solution become clear then added suitable substituted anilines (0.0039 mol), viz. 2-amino benzoic acid, 3-amino benzoic acid,4-amino benzoic acid, 4-amino salicylic acid, 5-amino salicylicacid, 2-amino-4-nitro benzoic acid, 3-amino-4-hydroxy benzoicacid, 5-amino-2-nitro benzoic acid, 3-amino-4-chloro benzoicacid, in the presence of slight excess of triethyl orthoformate (1 ml). The resultant reaction mixture was heated under reflux for 3-4 h. The solid product was collected by suction filtration in hot state. Then the product was washed with hot ethanol and dried. The products were obtained in good to excellent yields. The purity of the synthesized compounds was checked by thin layer chromatography using appropriate solvent systems (Methanol/Chloroform; 1:1). 4.2.22 5-([5-Nitro-2-(trifluoromethyl)phenyl]amino}methylidene)pyrimidine-2,4,6(1H,3H,5H)-trione (22) Yield 78%, yellow solid, mp 333-338 C (decompose) ; 1H NMR (d6-DMSO, δ, ppm); 12.62 (1H, d, J 12, =CHNH-), 11.29 (1H, s, CONHCO), 11.11 (1H, s, CONHCO), 8.76 (1H, d, J 12, =CH-N), 8.51 (1H, d, J 9.2 ArH), 8.42 (1H, s, ArH), 8.20 (1H, d, J 9.2, ArH), 13C NMR (d6-DMSO, δ, ppm): 166.8 (C), 162.7 (C), 151.3 (CH), 150.9 (C), 150.4(C), 143.38(C), 141.4 (C), 129.3 (CH), 122.8(CH), 120.7 (C), 120 (CH), 96.7 (C); MS (EI) m/z 334.2(M+ 100%), 314.2(6.8), 273.2(9.7), 171.1(4.6), 154.1(17.3), 144.1(13.2), 75.1(8.2), 69.1(10.7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In iso-butanol;Reflux; | General procedure: 0.5 g (0.0039 mol) of barbituric acid or thiobarbituric acid was added in 2-butanol (8-10 ml) and warmed till the solution become clear then added suitable substituted anilines (0.0039 mol), viz. 2-amino benzoic acid, 3-amino benzoic acid,4-amino benzoic acid, 4-amino salicylic acid, 5-amino salicylicacid, 2-amino-4-nitro benzoic acid, 3-amino-4-hydroxy benzoicacid, 5-amino-2-nitro benzoic acid, 3-amino-4-chloro benzoicacid, in the presence of slight excess of triethyl orthoformate (1 ml). The resultant reaction mixture was heated under reflux for 3-4 h. The solid product was collected by suction filtration in hot state. Then the product was washed with hot ethanol and dried. The products were obtained in good to excellent yields. The purity of the synthesized compounds was checked by thin layer chromatography using appropriate solvent systems (Methanol/Chloroform; 1:1). 4.2.31 5-([5-Nitro-2-(trifluoromethyl)phenyl]amino}methylidene)-2-thioxodihydropyri-midine-4,6(1H,5H)-dione (31) Yield 97%, light yellow solid, mp 308-312 C (decompose); 1H NMR (d6-DMSO, δ, ppm): 12.77 (1H, d, J 12, =CHNH-), 12.45 (1H, s, CONHCS), 12.28 (1H, s, CSNHCO), 8.81 (1H, d, J 12, =CH-N), 8.54 (1H, d, J 9.2, ArH), 8.48 (1H, s, ArH), 8.25 (IH, d, J 9.2, ArH); 13C NMR (d6-DMSO, δ, ppm): 178.2 (C), 164.7 (C), 160.8 (C), 152.6 (CH), 143.7(C), 141 (C), 129.2 (CH), 123.9(C), 122.8 (CH), 121.2 (C), 120.6 (CH), 97.7 (C); MS (EI) m/z 360.1(M+ 100%), 172.1(5), 155(30.5), 144.1(19.5), 116(11.1), 76.1(5.5), 69.1(9.8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.8% | With pyridine; In dichloromethane; at 0 - 20℃; | A mixture of <strong>[393-49-7]5-nitro-2-(trifluoromethyl)aniline</strong> (170 mg, 0.82 mmol) and pyridine (148 mg, 1.23 mmol) in DCM (4 mL) was added a solution of pentanoyl chloride (129 mg, 1.64 mmol) in DCM (2 mL) at 0C. After the mixture was stirred at room temperature overnight, the mixture was concentrated and purified by silica gel column chromatography (petroleum ether : ethyl acetate = 73:27) to give N-(5-nitro-2-(trifluoromethyl)- phenyl)pentanamide as a white solid. Yield: (0.21 g, 87.8%). ES-MS [M+H]+: 291.1 (Method-E). NMR (400 MHz, DMSO-d): d 9.84 ( 1 H, s), 8.37 ( 1 H, s), 8.21 (1 H, d, J = 8.8 Hz), 8.04 (1 H, d, J= 8.8 Hz), 2.41 (2 H, t, J= 7.2 Hz), 1.60-1.57 ( 2 H, m). 1.36-1.31 ( 2 H, m), 0.90 (3 H, t, J= 7.2 Hz). |
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