Structure of 838-77-7
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CAS No. : | 838-77-7 |
Formula : | C13H11ClN2O |
M.W : | 246.69 |
SMILES Code : | O=C(NC1=CC=CC=C1Cl)C2=CC=CC=C2N |
MDL No. : | MFCD00748574 |
Boiling Point : | No data available |
InChI Key : | WFSUBNNPXUDKAD-UHFFFAOYSA-N |
Pubchem ID : | 720820 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
In toluene; at 100℃; for 12h; | General procedure: 7.1.13. Solution-phase synthesis of library compounds 21Isatoic anhydride (20) (0.1 mmol) was partitioned into reaction vials and treated with aniline (0.10 mmol) in toluene (1.0 mL) at 100 C for 12 h. The mixture in each vessel was allowed to coolto ambient temperature, and the solvent was removed under reduced pressure. The residue in each vessel was dissolved in pyridine(1.0 mL) and treated with compound 37 (0.10 mol) at ambient temperature for 12 h. The mixture was then treated with polymer-bound tris(2-aminoethyl)amine for 12 h and filtered off. The filtrate was collected in vials and the solutions were evaporatedin vacuo to afford anthranilamide derivatives 21, which were analyzed by HPLC and MS. 21a; FAB-MS m/z 443 [M+H]+, 21b; FABMS m/z 443 [M+H]+, 21c; FAB-MS m/z 443 [M+H]+, 21d; FAB-MS m/z 463 [M+H]+, 21e; FAB-MS m/z 463 [M+H]+, 21g; FAB-MS m/z459 [M+H]+, 21h; FAB-MS m/z 489 [M+H]+, 21i; FAB-MS m/z 493[M+H]+, 21j; FAB-MS m/z 513 [M+H]+, 21k; FAB-MS m/z 521[M+H]+, 21l; FAB-MS m/z 472 [M+H]+, 21m; FAB-MS m/z 457 [M+H]+, 21n; FAB-MS m/z 471 [M+H]+, 21o; FAB-MS m/z 430[M+H]+, 21p; FAB-MS m/z 444 [M+H]+, 21q; FAB-MS m/z 444[M+H]+, 21r; FAB-MS m/z 444 [M+H]+, 21s; FAB-MS m/z 460 [M+H]+, 21t; FAB-MS m/z 449 [M]+, 21u; FAB-MS m/z 433[M+H]+, 21v; FAB-MS m/z 469 [M+H]+, 21w; FAB-MS m/z 480[M+H]+. Compound 21f was obtained from 2-amino-5-chloro-3-hydroxy-40-methoxybenzanilide using the methods described forthe synthesis of compound 19 as a colorless solid (423 mg, 56%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: 7.1.13. Solution-phase synthesis of library compounds 21Isatoic anhydride (20) (0.1 mmol) was partitioned into reaction vials and treated with aniline (0.10 mmol) in toluene (1.0 mL) at 100 C for 12 h. The mixture in each vessel was allowed to coolto ambient temperature, and the solvent was removed under reduced pressure. The residue in each vessel was dissolved in pyridine(1.0 mL) and treated with compound 37 (0.10 mol) at ambient temperature for 12 h. The mixture was then treated with polymer-bound tris(2-aminoethyl)amine for 12 h and filtered off. The filtrate was collected in vials and the solutions were evaporatedin vacuo to afford anthranilamide derivatives 21, which were analyzed by HPLC and MS. 21a; FAB-MS m/z 443 [M+H]+, 21b; FABMS m/z 443 [M+H]+, 21c; FAB-MS m/z 443 [M+H]+, 21d; FAB-MS m/z 463 [M+H]+, 21e; FAB-MS m/z 463 [M+H]+, 21g; FAB-MS m/z459 [M+H]+, 21h; FAB-MS m/z 489 [M+H]+, 21i; FAB-MS m/z 493[M+H]+, 21j; FAB-MS m/z 513 [M+H]+, 21k; FAB-MS m/z 521[M+H]+, 21l; FAB-MS m/z 472 [M+H]+, 21m; FAB-MS m/z 457 [M+H]+, 21n; FAB-MS m/z 471 [M+H]+, 21o; FAB-MS m/z 430[M+H]+, 21p; FAB-MS m/z 444 [M+H]+, 21q; FAB-MS m/z 444[M+H]+, 21r; FAB-MS m/z 444 [M+H]+, 21s; FAB-MS m/z 460 [M+H]+, 21t; FAB-MS m/z 449 [M]+, 21u; FAB-MS m/z 433[M+H]+, 21v; FAB-MS m/z 469 [M+H]+, 21w; FAB-MS m/z 480[M+H]+. Compound 21f was obtained from 2-amino-5-chloro-3-hydroxy-40-methoxybenzanilide using the methods described forthe synthesis of compound 19 as a colorless solid (423 mg, 56%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | To a solution of anthranilic acid (147 mg, 1.07 mmol) in THF (10 mL) was added SOCl2 (2.0 mL). The mixture was stirred at r.t. for 1 h, and then 2-chloroaniline (255 mg, 2.00 mmol) in pyridine (1.0 mL) was added. The whole was stirred at r.t. overnight, then diluted with AcOEt and the organic layer was washed with H2O and brine, dried and concentrated. Column chromatography (n-hexane : AcOEt=5 : 1 to 3 : 1) of the residue gave the title compound (203 mg, 0.821 mmol, 76%) as a yellow solid. 1H-NMR (500 MHz, CDCl3) δ: 8.45 (1H, d, J=7.9 Hz), 8.34 (1H, br s), 7.54 (1H, d, J=8.0 Hz), 7.41 (1H, d, J=7.9 Hz), 7.34-7.27 (2H, m), 7.09-7.06 (1H, m), 6.76-6.73 (1H, m), 5.60 (2H, br s). FAB-MS m/z 246 (M+), 247 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20℃; for 15.5h; | General procedure: To a solution of 3 (80.6 mg, 260 μmol) and CS2 (300 μL, 5.00 mmol) in DMF (2.0 mL) was added DBU (38.7 μL, 258 μmol). The reaction mixture was stirred for 15.5 h at r.t., and then diluted with AcOEt. The organic layer was washed with 2 N HCl aq, water and brine, then dried and concentrated to afford the title compound (87.7 mg, 0.248 mmol, 96%) as a pale yellow solid (recrystallized from CHCl3/MeOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(I) oxide; tricyclohexylphosphine; In chloroform; at 100℃; for 24h;Schlenk technique; Sealed tube; | General procedure: A reaction tube was charged under air with 2-aminobenzanilide(1a, 0.2 mmol), Et3N (2a, 0.6 mmol), Cu2O (10 mol%), PCy3(10 mol%), and CHCl3 (2 mL). The vessel was sealed, heated at100 C (oil-bath temperature) for 24 h, and then cooled to r.t.DDQ (1 equiv) was added, and the mixture was kept at r.t. for 1h. After filtration of the mixture and evaporation of the solventunder reduced pressure, the crude product was purified by column chromatography [silica gel, hexane-EtOAc (3:1)] to givea light-yellow solid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tert.-butylnitrite; saccharin; In ethanol; at 50℃; for 6h;Green chemistry; | General procedure: Initially, 2-amino-N-(arylphenyl)-benzamide (0.484 g, 2.0mmol) (1) was added with slow stirring to a mixture of Sac-H (0.037 g, 0.2mmol) and tert-butyl nitrite (0.40mL, ,3.0mmol) in dry ethanol (5mL) for 5 min at room temperature. Then, stirring was continued for 6 h. The solvent, by-product tert-BuOH, and excess tert-BuONO were evaporated under reduced pressure after completion of the reaction (monitored by TLC). The crude residue was purified by column chromatography on silica gel with light petroleum/ethyl acetate (8 : 2 to 7 : 3 v/v) to give the pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In a closed quartz reaction tube,Add ethanol (0.6mmOl),Photosensitizer fluorescein (2.5mmol%) and DMF (2mL),Under the illumination of a xenon lamp (320~720nm),Reacting under oxygen at 24 C for 20 h;Then, <strong>[838-77-7]2-amino-N-(2-chlorophenyl)benzamide</strong> (0.2 mmol) and trifluoroacetic acid (4 mmol%) were added to the quartz reaction tube.Under the illumination of a gas lamp (320~720nm),Reacted in oxygen at 24 C for 24 h,After the reaction is over,Vacuum distillation,Column chromatography separation (ΕΑ: PE = 1:8),Obtaining the target compound in the form of a yellow liquid,The yield was 96%.Nuclear magnetic resonance spectrum of the target compound 3-(2-chlorophenyl)-2-methylquinazolin-4(3H)-one |
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